This application is a 371 of PCT/JP00/02764 Apr. 17, 2000.
This invention relates to sulfonamide derivatives useful as microbicides for agricultural or horticultural use.
A lot of microbicides have ever been synthesized and used as microbicides for agriculture or horticulture. They have contributed greatly to supply agricultural products constantly. However, it is well-known that frequent use of restricted number of compounds has led to outbreak of microbes which are resistant to those drugs. In addition, recent rise in demand for the safety and environmental influence of chemical substances has made it desirable to develop safer microbicides for agricultural or horticultural use. This has given an intention to the researches to explore and research novel compounds with microbicidal activity. As for sulfonamide derivatives, a lot of compounds have also been synthesized so far from the interests in their biological or chemical characteristics. A majority of them are, however, synthetic intermediates, medicines, compounds prepared for the aim of elucidating chemical reaction mechanism or reagents. As for sulfonamide derivatives related to microbicides, there may be cited those described in Japanese Patent Publication for Laid-Open 286366/1986, Japanese Patent Publication for Laid-Open 239264/1988, Japanese Patent Publication for Laid-Open 238006/1988, Japanese Patent Publication for Laid-Open 307851/1988, Japanese Patent Publication for Laid-Open 156952/1989, and in J. Med. Chem. 1983, 26, 1741, and in DE19725447, and so on.
Nevertheless, no sulfonamide derivative has been developed yet, which is safe and has little influence on human beings and firm animals, natural enemies, and the environment, and exert excellent protective effects even on drug-resistant microbes.
The present inventors have made intensive efforts for many years in order to find out compounds which have excellent microbicidal action and solve the problems mentioned above. As the results, they have found that the compounds represented by the formula I0 or salts thereof.
Formula I0: 
[wherein, A0 is (1) an aryl group which may be substituted, or (2) a heterocyclic group which may be substituted, X0 is (1) a chemical bond, (2) a methylene group which may be substituted or (3) a vinylene group which may be substituted, B0 is a heterocyclic group which may be substituted or an aryl group which may be substituted, Z0 is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which maybe substituted, (5) xe2x80x94Nxe2x95x90CR1R2(wherein R1 and R2is a hydrogen atom or a hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) xe2x80x94OR3(wherein R3 is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or an alkylsulfonyl group which may be substituted), or (8) a xe2x80x94S(O)nR4(wherein n represents an integer from 0 to 2, and R4 is a hydrogen atom or a hydrocarbon group which may be substituted)], (hereafter, they may also be mentioned as compounds (I0)), or more specifically compounds (I) to (V)(as will be stated below) or salts thereof have unexpectedly a very strong microbicidal activity, while, on the contrary, they revealed only a low toxicity to human being and farm animals, fishes and natural enemies. The present inventors carried out an intensive research based on these findings and have completed the present invention. Thus, the present invention relates to:
[1] A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (I): 
or a salt thereof
[wherein A1 is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X1 is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted, B1 is a five-membered heterocyclic group (except for an isoxazolyl group) or a condensed heterocyclic group which may be substituted, Z1 is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group which is represented by xe2x80x94Nxe2x95x90CR1R2(wherein each R1 and R2 is respectively a hydrogen atom or a hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group which is represented by xe2x80x94OR3 (wherein R3 is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or an alkylsulfonyl group which may be substituted) or (8) a group represented by xe2x80x94S(O)nR4 (wherein, n stands for an integer from 0 to 2, R4 stands for a hydrogen atom or a hydrocarbon group which may be substituted).]
[2] A microbicidal composition for agricultural or horticultural use described in [1] above, wherein B1 is a five-membered heterocyclic group which contains hetero-atoms selected from nitrogen atoms and sulfur atoms as the ring-constructing hetero atom in addition to the carbon atoms which may be substituted, or B1 is a condensed heterocyclic group which may be substituted.
[3] A microbicidal composition described in [1] above, wherein A1 is (1) an aryl group which may be substituted with 1 to 5 substituents selected from a group of substituents (T) which consists of (i) a C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (ii) a C3-6 cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) a C2-4 alkenyl group which may be substituted with 1 to 5 substituents selected from halogen, cyano, and nitro, (iv) a C3-6 cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C2-4 alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxyl group, (vii) a C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogen and C1-4 alkoxy group, (viii) formyloxy group, (ix) a C1-4 alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C1-4 alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C1-4 alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C1-4 alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C1-4 alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) a sulfamoyl group, (xviii) a mono- or di-C1-4 alkylsulfamoyl group, (xix)a group represented by 
(wherein, ring C is a 3- to 6-membered heterocyclic group containing nitrogen), (xx) an amino group which may be substituted with one or two substituents selected from a C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, hydroxy, C1-4 alkoxy, formyloxy, C1-4 alkyl-carbonyloxy, formyl and C1-4 alkyl-carbonyl, (xxi) a 3- to 6-membered cyclic amino group, (xxii) formyl group. (xxiii) a C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) a C1-4 alkylthio-carbonyl group, (xxvi) a C1-4 alkoxy-thiocarbonyl group, (xxvii) C1-4 alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) a mono- or di-C1-4 alkylcarbamoyl group, (xxx) a group represented by 
(wherein, ring C is a 3- to 6-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) a mono- or di-C1-4 alkyl-thiocarbamoyl group, (xxxiii) a group represented by 
(wherein, ring C is a 3- to 6-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group, (xliv) azoxycyano group and (xlv) sulfo group, or (2) a heterocyclic group which may be substituted with 1 to 5 substituents selected from the group of substituents (T) mentioned above,
X1 is (1) a chemical bond, (2) a methylene group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen atom and cyano or (3) a vinylene group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen atom, and cyano, B1 is (1) a five-membered heterocyclic group which is composed of the ring-constructing heteroatoms besides carbon atoms selected from nitrogen and sulfur atoms, and which may be substituted with 1 to 5 substituents selected from the group of substituents (T) mentioned above, or (2) a condensed heterocyclic group which is constructed either with a five- to six-membered heterocyclic ring and benzene rings or with a five- to six-membered heterocyclic ring and another (the same or different) five- to six-membered heterocyclic rings and may be substituted with substituents selected from the group of substituents (T) mentioned above, Z1 is (1) a hydrocarbon group which is selected from (i) a C1-6 alkyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) a mono- or di-C1-4 alkyl-carbamoyl group, (ii) a C2-6 alkenyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl, and (m) mono- or di-C1-4 alkyl-carbamoyl, (iii) a C2-6 alkynyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl, and (m) mono- or di-C1-4 alkyl-carbamoyl, (iv) a C3-6 cycloalkyl group which may be substituted with 1 to 5 substituents selected from (a) C1-4 alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C1-4 alkylamino, (e) hydroxy, (f) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C1-4 alkylthio, (i) C1-4 alkylsulfinyl, (j) C1-4 alkylsulfonyl, (k) cyano, (1) C1-4 alkoxy-carbonyl, (m) carbamoyl, and (n) mono- or di-C1-4 alkyl-carbamoyl, (v) a C3-6 alkadienyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- and di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (l) carbamoyl and (m) mono- or di- C1-4 alkyl-carbamoyl or (vi) C6-14 aryl group which may be substituted with 1 to 5 substituents selected from (a) C1-4 alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C1-4 alkylamino, (e) hydroxy, (f) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C1-4 alkylthio, (i) C1-4 alkylsulfinyl, (j) C1-4 alkylsulfonyl, (k) cyano, (1) C1-4 alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C1-4 alkyl-carbamoyl, (2) an acyl group selected from (i) C1-4 alkyl-carbonyl, (ii) C1-4 alkoxy-carbonyl, (iii) C1-4 alkylthio-carbonyl, (iv) C1-4 alkoxy-thiocarbonyl, (v) C1-4 alkylthio-thiocarbonyl, (vi) mono- or di-C1-4 alkyl-carbamoyl and (vii) mono- or di-C1-4 alkyl-thiocarbamoyl, each of which may be substituted with 1 to 5 halogens, (3) formyl group, (4) an amino group which may be substituted with one or two substituents selected from (a) C1-4 alkyl, (b) C1-4 alkyl-carbonyl which may be substituted with 1 to 5 halogens, (c) C1-4 alkoxy-carbonyl, (d) mono- or di-C1-4 alkyl-carbamoyl and (e) mono- or di-C1-4 alkyl-thiocarbamoyl, (5) a group represented by xe2x80x94Nxe2x95x90CR1R2(wherein R1 and R2 are the same or different, and are a hydrogen atom and a C1-4 alkyl group), (6) a three- to six-membered cyclic amino group, (7) a group represented by xe2x80x94OR3 (wherein R3 is a hydrogen atom, a C1-4 alkyl group which may be substituted with 1 to 5 halogens, a C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, formyl group or a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens), or (8) a group represented by xe2x80x94S(O)nR4 (wherein n is an integer from 0 to 2, and R4 is (a) a hydrogen atom, (b) a C1-4 alkyl group which may be substituted with 1 to 5 halogens or (c) a C6-14 aryl group which may be substituted with 1 to 5 C1-4 alkyl groups.
[4] A microbicidal composition for agricultural or horticultural use described in [1] above, where A1 is a C6-14 aryl group which may be substituted with 1 to 3 alkyl group, X1 is a chemical bond, B1 is a thienyl group, a pyrazolyl group, an isothiazolyl group, an imidazolyl group, a thiazolyl group, a thiadiazolyl group, a dioxaindanyl group or an imidazopyridyl group, each of which may be substituted with 1 to 5 substituents selected from C1-4 alkyl which may be substituted with 1 to 5 halogens, C1-4 alkoxy, C1-4 alkylthio, cyano, halogens and nitro, Z1 is a C1-6 alkyl group or a C1-4 alkoxy group.
[5] A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (II): 
or a salt thereof,
[wherein, A2 is (1)an aryl group which may be substituted with 1 to 5 substituents selected from a group of substituents (Txe2x80x2) which consists of (i) a C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogen, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (ii) a C3-6 cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) a C2-4 alkenyl group which may be substituted with substituents selected from halogens, cyano and nitro, (iv) a C3-6 cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C2-4 alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) a C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy, (viii) formyloxy group, (ix) a C1-4 alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C1-4 alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C1-4 alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C1-4 alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C1-4 alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C1-4 alkylsulfamoyl group, (xix) a group represented by 
xe2x80x83(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) an amino group which may be mono- or disubstituted with one or two substituents selected from C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, hydroxy, C1-4 alkoxy, formyloxy, C1-4 alkyl-carbonyloxy, formyl and C1-4 alkyl-carbonyl, (xxi) a three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) a C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) a C1-4 alkylthio-carbonyl group, (xxvi) a C1-4 alkoxy-thiocarbonyl group, (xxvii) a C1-4 alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) a mono- or di-C1-4 alkylcarbamoyl group, (xxx) a group represented by 
xe2x80x83(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) a mono- or di-C1-4 alkyl-thiocarbamoyl group, (xxxiii) a group represented by 
xe2x80x83(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group and (xliv) sulfo group or (2) a heterocyclic group, which may be substituted.
X2 is (1) a chemical bond, (2) a methylene group which may be substituted or (3) a vinylene group which may be substituted, B2 is an aryl group which may be substituted, Z2 is (1) an alkyl group which may be substituted with substituents selected from mono- or di-C1-6 alkylamino, hydroxy, halogens, C1-6 alkoxy, C1-6 alkoxy-carbonyl, C1-6 alkylthio and cyano, (2) vinyl group, (3) an allyl group, (4) a propadienyl group, (5) an alkynyl group which may be substituted, (6) a cycloalkyl group which may be substituted, (7) an aryl group which may be substituted, (8) an acyl group which may be substituted, (9) formyl group, (10) an amino group which may be substituted, (11) a group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein R1 and R2 are the same or different, and are a hydrogen atom and a hydrocarbon group which may be substituted respectively), (12) a cyclic amino group, (13) a group represented by xe2x80x94OR3 (wherein R3 is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group, or an alkylsulfonyl group which may be substituted), or (14) a group represented by xe2x80x94S(O)nR4 (wherein, n is an integer from 0 to 2, and R4 is a hydrogen atom or a hydrocarbon group which may be substituted).
[6] A microbicidal composition for agricultural or horticultural use described in [5] above, [wherein, A2 is (1)a C6-14 aryl group which may be substituted with 1 to 5 substituents selected from a group of substituents (Txe2x80x2) which consists of (i) a C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogen, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (ii) a C3-6 cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) C2-4 alkenyl group which may be substituted with 1 to 5 substituents selected from halogens, cyano and nitro, (iv) a C3-6 cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C2-4 alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) a C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy, (viii) formyloxy group, (ix) a C1-4 alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C1-4 alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C1-4 alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C1-4 alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C1-4 alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xi) a C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C1-4 alkylsulfamoyl group, (xix) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) an amino group which may be substituted with one or two substituents selected from C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, hydroxy, C1-4 alkoxy, formyloxy, C1-4 alkyl-carbonyloxy, formyl and C1-4 alkyl-carbonyl, (xxi) a three to six-membered cyclic amino group, (xxii) formyl group, (xxiii) a C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) a C1-4 alkylthio-carbonyl group, (xxvi) a C1-4 alkoxy-thiocarbonyl group, (xxvii) a C1-4 alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) a mono- or di-C1-4 alkylcarbamoyl group, (xxx) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group (xxxii) a mono- or di-C1-4 alkyl-thiocarbamoyl group, (xxxiii) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group and (xliv) sulfo group, or (2) heterocyclic group which may be substituted with 1 to 5 substituents selected from a group of substituents (T) which consists of (i) C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (ii) a C3-6 cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) C2-4 alkenyl group which may be substituted with 1 to 5 substituents selected from halogens, cyano and nitro, (iv) C3-6 cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C2-4 alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy, (viii) formyloxy group, (ix) C1-4 alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) C1-4 alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (Xii) C1-4 alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C1-4 alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C1-4 alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C1-4 alkylsulfamoyl group, (xix) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) an amino group which may be substituted with one or two substituents selected from C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, hydroxy, C1-4 alkoxy, formyloxy, C1-4 alkyl-carbonyloxy, formyl and C1-4 alkyl-carbonyl, (xxi) three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) C1-4 alkylthio-carbonyl group, (xxvi) a C1-4 alkoxy-thiocarbonyl group, (xxvii) C1-4 alkylthio-thiocarbonyl group, (xxviii) a carbamoyl group, (xxix) mono- or di-C1-4 alkylcarbamoyl group, (xxx) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) mono- or di-C1-4 alkyl-thiocarbamoyl group, (xxxiii) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group and (xliv) azoxycyano group, and (xlv) sulfo group, X2 is (1) a chemical bond, (2) a methylene group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen atoms, and cyano, or (3) a vinylene group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen atoms and cyano, B2 is an aryl group which may be substituted with 1 to 5 substituents selected from the group of substituents (T) described above, Z2 is (1) C1-6 alkyl group which may be substituted with 1 to 5 substituents selected from mono- or di-C1-4 alkylamino, hydroxy, halogen, C1-4 alkoxy, C1-4 alkoxy-carbonyl, C1-4 alkylthio and cyano, (2) vinyl group, (3) allyl group, (4) propadienyl group, (5) C2-6 alkynyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) a C1-4 alkoxy substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy- carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, (6) C3-6 cycloalkyl group which may be substituted with 1 to 5 substituents selected from (a) C1-4 alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C1-4 alkylamino, (e) hydroxy, (f) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C1-4 alkylthio, (i) C1-4 alkylsulfinyl, (j) C1-4 alkylsulfonyl, (k) cyano, (1) C1-4 alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C1-4 alkyl-carbamoyl, (7) C6-14 aryl group which may be substituted with 1 to 5 substituents selected from (a) C1-4 alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C1-4 alkylamino, (e) hydroxy, (f) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C1-4 alkylthio, (i) C1-4 alkylsulfinyl, (j) C1-4 alkylsulfonyl, (k) cyano, (1) C1-4 alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C1-4 alkyl-carbamoyl, (8) acyl group selected from (i) C1-4 alkyl-carbonyl, (ii) C1-4 alkoxy-carbonyl, (iii) C1-4 alkylthio-carbonyl, (iv) C1-4 alkoxy-thiocarbonyl, (v) C1-4 alkylthio-thiocarbonyl, (vi) mono- or di-C1-4 alkyl-carbamoyl and (vii) mono- or di-C1-4 alkyl-thiocarbamoyl, each of which may be substituted with 1 to 5 halogens, (9) formyl group, (10) amino group which may be substituted with one or two substituents selected from (a) C1-4 alkyl, (b) C1-4 alkyl-carbonyl which may be substituted with 1 to 5 halogens, (c) C1-4 alkoxy-carbonyl, (d) mono- or di-C1-4 alkyl-carbamoyl and (e) mono- or di-C1-4 alkyl-thiocarbamoyl, (11) a group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein R1 and R2 are the same or different, and are a hydrogen atom and a C1-4 alkyl group), (12) three- to six-membered cyclic amino group, (13) a group represented by xe2x80x94OR3 (wherein R3 is a hydrogen atom, a C1-4 alkyl group which may be substituted with 1 to 5 halogens, a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, formyl group, or C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens), or (14) a group represented by xe2x80x94S(O) R4 (wherein n is an integer from 0 to 2, and R4 is (a) hydrogen atom, (b) C1-4 alkyl group which may be substituted with 1 to 5 halogens or (c) C6-14 aryl group which may be substituted with 1 to 5 C1-4 alkyl groups).
[7] A microbicidal composition for agricultural or horticultural use described in [5] above, wherein A2 is (1) C6-14 aryl group, which may be substituted with 1 to 5 substituents selected from (i) C1-4 alkyl group which may be substituted with 1 to 5 halogens, (ii) C1-4 alkoxy group which may be substituted with 1 to 5 halogens, (iii) amino group which may be substituted with one or two C1-4 alkyl-carbonyl group, (iv) C1-4 alkoxy-carbonyl group, (v) halogen atom, (vi) cyano group and (vii) nitro group, or (2) thienyl group, triazolyl group, imidazolyl group, isoxazolyl group, pyrazolyl group, pyridyl group, quinolyl group, benzothiadiazolyl group, imidazothiazolyl group or imidazopyridyl group, which may be substituted with 1 to 5 substituents selected from (i) C1-4 alkyl group, (ii) C1-4 alkoxy-carbonyl group, (iii) carbamoyl group, (iv) mono- or di-C1-4 alkylcarbamoyl group, (v) C1-4 alkylsulfonyl group, (vi) halogen atom, (vii) carboxyl group and (viii) cyano group, X2 is (1) a chemical bond, (2) a methylene group which may be substituted with one or two C1-4 alkyl group, or (3) a vinylene group which may be substituted with one or two C1-4 alkyl, B2 is a C6-14 aryl group which may be substituted with 1 to 5 substituents selected from (1) a C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogen, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono,mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (2) C2-4 alkynyl group, (3) hydroxy group, (4) a C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy, (5) a C1-4 alkyl-carbonyloxy group, (6) a C1-4 alkylthio group, (7) a C1-4 alkylsulfinyl group, (8) a C1-4 alkylsulfonyl group, (9) mono- or di-C1-4 alkylsulfamoyl group, (10) amino group, (11) formyl group, (12) C1-4 alkoxy-carbonyl group, (13) carbamoyl group, (14) mono- or di-C1-4 alkylcarbamoyl group, (15) thiocarbamoyl group, (16) halogen atom, (17) carboxyl group, (18) thiocyanato group, (19) cyano group, (20) nitroso group and (21) nitro group, Z2 is (1) a C1-6 alkyl group which may be substituted with 1 to 5 substituents selected from mono- or di-C1-4 alkylamino, hydroxy, halogen, C1-4 alkoxy, C1-4 alkoxy-carbonyl, C1-4 alkylthio and cyano, (2) vinyl group, (3) allyl group, (4) propadienyl group, (5) C2-6 alkynyl group which may be substituted with 1 to 5 halogens, (6) C3-6 cycloalkyl group, (7) C6-14 aryl group, (8) C1-4 alkyl-carbonyl which may be substituted with 1 to 5 halogens, (9) an amino group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkyl-carbonyl and C1-4 alkoxy-carbonyl, (10) a group represented by xe2x80x94Nxe2x95x90CR1R2(wherein, both R1 and R2 are the same or different C1-4 alkyl groups), (11) a group represented by xe2x80x94OR3 (wherein R3 is a C1-4 alkyl group or a C1-4 alkyl-carbonyl group), or (12) a group represented by xe2x80x94S(O)nR4 (wherein n is an integer from 0 to 2, R4 is (a) a C1-4 alkyl group which may be substituted with 1 to 5 halogens, or (b) a C6-14 aryl group which may be substituted with 1 to 5 C1-4 alkyl groups).
[8] A microbicidal composition for agricultural or horticultural use described in (5] above, wherein
A2 is a phenyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl groups, halogens and cyano,
X2 is a chemical bond,
B2 is a phenyl group which may be substituted with 1 to 5 substituents selected from (1) a C1-4 alkyl group which may be substituted with 1 to 3 halogens, (2) C1-4 alkoxy group, (3) C1-4 alkylthio group, (4) thiocarbamoyl group, (5) halogen atom, (6) cyano group and (7) nitro group, Z2 is (1) a C1-6 alkyl group which may be substituted with 1 to 3 C1-4 alkoxy groups, (2) C3-6 cycloalkyl group, (3) allyl group or (4) C1-4 alkoxy group.
[9] A microbicidal composition for agricultural or horticultural use described in [5] above, wherein the compound or the salt thereof is 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 2xe2x80x2,4xe2x80x2-dinitro-N-ethyl-p-toluenesulfonanilide, 2xe2x80x2,4xe2x80x2-dicyano-N-ethyl-p-toluenesulfonanilide, 4xe2x80x2-chloro-N-isopropyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 4xe2x80x2-fluoro-N-isopropyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 4xe2x80x2-cyano-N-isopropyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 4xe2x80x2-chloro-N-isopropyl-2xe2x80x2-cyano-p-toluenesulfonanilide, 2,4xe2x80x2-dinitro-N-isopropyl-p-toluenesulfonanilide, 2xe2x80x2-cyano-N-isopropyl-4xe2x80x2-nitro-p-toluenesulfonanilide, 2xe2x80x2-cyano-N-methoxy-4xe2x80x2-nitro-p-toluenesulfonanilide or 2xe2x80x2,4xe2x80x2- dinitro-N-methoxy-p-toluenesulfonanilide or a salt thereof.
[10] A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (III): 
or a salt thereof,
(wherein, A3 is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X3is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted,
B3 is a six-membered heterocyclic group which is substituted with substituents selected from the group of substituents (T), which consists of (i) a C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogen,hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (ii) a C3-6 cycloalkyl group which may be substituted with 1 to 5 halogen, (iii) a C2-4 alkenyl group which may be substituted with 1 to 5 substituents selected from halogens, cyano and nitro, (iv) a C3-6 cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C2-4 alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) a C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogen and C1-4 alkoxy group, (viii) formyloxy group, (ix) C1-4 alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C1-4 alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C1-4 alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C1-4 alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C1-4 alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C1-4 alkylsulfamoyl group, (xix) a group represented by 
xe2x80x83(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) an amino group which may be substituted with one or two substituents selected from C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, hydroxy, C1-4 alkoxy, formyloxy, C1-4 alkyl-carbonyloxy, formyl and C1-4 alkyl-carbonyl, (xxi) a three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) a C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) a C1-4 alkylthio-carbonyl group, (xxvi) a C1-4 alkoxy-thiocarbonyl group, (xxvii) a C1-4 alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) a mono- or di-C1-4 alkylcarbamoyl group, (xxx) a group represented by 
xe2x80x83(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) mono- or di-C1-4 alkyl-thiocarbamoyl group, (xxxiii) a group which is represented by 
xe2x80x83(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group (xliv) azoxycyano group, and (xlv) sulfo group,
Z3 is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein, R1 and R2 are the same or different, and a hydrogen atom or a hydrocarbon group which may be substituted), (6) cyclic amino group, (7) a group represented by xe2x80x94OR3 (wherein, R3 stands for a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or sulfonyl group which may be substituted), or (8) a group represented by xe2x80x94S(O)nR4 (wherein, n is an integer from 0 to 2, R4 is a hydrogen atom or a hydrocarbon group which may be substituted)].
[11] A microbicidal composition for agricultural or horticultural use described in [10] above, wherein A3 is (1) C6-14 aryl group which may be substituted with 1 to 5 substituents selected from (i) C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (ii) C3-6 cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) C2-4 alkenyl group which may be substituted with 1 to 5 substituents selected from halogens, cyano and nitro, (iv) C3-6 cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) C2-4 alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy, (viii) formyloxy group, (ix) C1-4 alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) C1-4 alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) C1-4 alkylthio group which may be substituted with 1 to 5 halogens, (xiii) C1-4 alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) C1-4 alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) mono- or di-C1-4 alkylsulfamoyl group, (xix) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) amino group which may be substituted with one or two substituents selected from C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, hydroxy, C1-4 alkoxy, formyloxy, C1-4 alkyl-carbonyloxy, formyl and C1-4 alkyl-carbonyl, (xxi) three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) C1-4 alkylthio-carbonyl group, (xxvi) C1-4 alkoxy-thiocarbonyl group, (xxvii) C1-4 alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) mono- or di-C1-4 alkylcarbamoyl group, (xxx) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) mono- or di-C1-4 alkyl-thiocarbamoyl group, (xxxiii) a group represented by 
(wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group (xliv) azoxycyano group, and (xlv) sulfo group, or (2) a heterocyclic group which may be substituted with 1 to 5 substituents selected from the group of substituents (T) above.
X3 is (1) chemical bond, (2) methylene group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen atoms and cyano, (3) a vinylene group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen atoms and cyano,
B3 is a six-membered heterocyclic group which is substituted with 1 to 5 substituents selected from the group of substituents (T) mentioned above, Z3 is (1) a hydrocarbon group which is selected from (i) a C1-6 alkyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (J) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, (ii) C2-6 alkenyl which may be substituted with 1 to 5 substituents selected from (a) halogens, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, (iii) C2-6 alkynyl which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, (iv) C3-6 cycloalkyl groups which may be substituted with 1 to 5 substituents selected from (a) C1-4 alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C1-4 alkylamino, (e) hydroxy, (f) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C1-4 alkylthio, (i) C1-4 alkylsulfinyl, (j) C1-4 alkylsulfonyl, (k) cyano, (1) C1-4 alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C1-4 alkyl-carbamoyl, (v) C3-6 alkadienyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, and (vi) C6-14 aryl group which may be substituted with 1 to 5 substituents selected from C1-4 alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C1-4 alkylamino, (e) hydroxy, (f) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C1-4 alkylthio, (i) C1-4 alkylsulfinyl, (j) C1-4 alkylsulfonyl, (k) cyano, (1) C1-4 alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C1-4 alkyl-carbamoyl, (2) an acyl group selected from (i) C1-4 alkyl-carbonyl, (ii) C1-4 alkoxy-carbonyl, (iii) C1-4 alkylthio-carbonyl, (iv) C1-4 alkoxy-thiocarbonyl, (v) C1-4 alkylthio-thiocarbonyl, (vi) mono- or di-C1-4 alkyl-carbamoyl and (vii) mono- or di-C1-4 alkyl-thiocarbamoyl, each of these groups may be substituted with 1 to 5 halogens, (3) formyl group, (4) an amino group which may be substituted with one or two substituents selected from (a) C1-4 alkyl, (b) C1-4 alkyl-carbonyl which may be substituted with 1 to 5 halogens, (c) C1-4 alkoxy-carbonyl, (d) mono- or di-C1-4 alkyl-carbamoyl, (e) mono- or di-C1-4 alkyl-thiocarbamoyl, (5) a group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein, R1 and R2 are the same or different, are a hydrogen atom or a C1-4 alkyl group), (6) three-to six-membered cyclic amino group, (7) a group represented by xe2x80x94OR3 (wherein, R3 is a hydrogen atom, a C1-4 alkyl group which may be substituted with 1 to 5 halogens, a C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, formyl group or a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens), or (8) a group represented by xe2x80x94S(O)nR4 (wherein n is an integer from 0 to 2, R4 is (a) hydrogen atom, (b) C1-4 alkyl group which may be substituted with 1 to 5 halogens, or (c) C6-14 aryl group which may be substituted with 1 to 5 C1-4 alkyl groups).
[12] A microbicidal composition for agricultural or horticultural use described in [10] above, wherein A3 is phenyl group which may be substituted with 1 to 5 C1-4 alkyl groups, or an imidazolyl group which may be substituted with one or two C1-4 alkyl groups, X3 is a chemical bond, B3 is a pyridyl group, a pyridazinyl group or a pyrimidinyl group which is substituted with 1 to 5 substituents selected from C1-4 alkyl which may be substituted with 1 to 5 halogens, C1-4 alkoxy, halogen, nitro and cyano, Z3 is a C1-6 alkyl group, a C3-6 cycloalkyl group or a C1-4 alkoxy group.
[13] A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (IV) 
or a salt thereof, [wherein, A4 is (1) an aryl group which may be substituted, or (2) a heterocyclic group which may be substituted,
X4 is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted,
B4 is a pyridazinyl group or a pyrazinyl group,
Z4 is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein R1 and R2 are the same or different, and hydrogen atom or hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group represented by xe2x80x94OR3 (wherein, R3 is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or a sulfonyl group which may be substituted), or (8) a group represented by xe2x80x94S(O)nR4 (wherein, n is an integer from 0 to 2, R4 is a hydrogen atom or a hydrocarbon group which may be substituted)].
[14] A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (V) 
or a salt thereof,
[wherein A5 is the 4-methylphenyl group, X5 is a chemical bond, B5 is a pyridyl or pyrimidinyl group, and Z5 is a C1-4 alkyl group].
[15] A compound of Formula (VI): 
or a salt thereof,
[wherein A6 is a phenyl group which may be substituted with a substituent or substituents selected from C1-4 alkyl, halogens and cyano, X6 is a chemical bond, B6 is a 2-nitrophenyl group or a 2-cyanophenyl group which is substituted with a substituent or substituents selected from halogens, nitro and cyano, Z6 is ethyl, isopropyl, cyclopropyl, methoxy, ethoxy or isopropoxy group].
[16] A compound or a salt thereof described in [15] above, wherein A6 is a phenyl group which may be substituted with a substituent or substituents selected from C1-4 alkyl, halogens and cyano, X6is a chemical bond, B6 is a 2-nitrophenyl group which is substituted with a substituent or substituents selected from halogens, nitro and cyano, Z6 is ethyl, isopropyl, or cyclopropyl group].
[17] A compound or a salt thereof described in [15] above, the compound is 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 2xe2x80x2,4xe2x80x2-dinitro-N-ethyl-p-toluenesulfonanilide, 2xe2x80x2,4xe2x80x2-dicyano-N-ethyl-p-toluenesulfonanilide, 4xe2x80x2-chloro-N-isopropyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 4xe2x80x2-fluoro-N-isopropyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 4xe2x80x2-cyano-N-isopropyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 4xe2x80x2-chloro-N-isopropyl-2xe2x80x2-cyano-p-toluenesulfonanilide, 2xe2x80x2,4xe2x80x2-dinitro-N-isopropyl-p-toluenesulfonanilide, 2xe2x80x2-cyano-N-isopropyl-4xe2x80x2-nitro-p-toluenesulfonanilide, 2xe2x80x2-cyano-N-methoxy-4xe2x80x2-nitro-p-toluenesulfonanilide or 2xe2x80x2,4xe2x80x2- dinitro-N-methoxy-p-toluenesulfonanilide or a salt thereof.
[18] A method for manufacturing a compound represented by a Formula: 
or a salt thereof (wherein each symbol has the same meaning as defined in [15] above characterized by:
(1) reacting a compound represented by a Formula: 
or a salt thereof
(wherein each symbol has the same meaning as defined in [15] above with an electrophile represented by Formula Z6xe2x80x94Lxe2x80x3 (wherein Lxe2x80x3 is a leaving group, and Z6 has the same meaning as defined in [15] above,
(2) reacting a compound represented by a Formula:
A6xe2x80x94X6xe2x80x94SO2xe2x80x94L
or a salt thereof,
(wherein L is a leaving group, and each of other symbols has the same meanings as those defined in [15] above, respectively) with an amine or a salt thereof represented by Formula Z6HNxe2x80x94B6 (wherein each symbol has the same meaning as defined in [15] above, or, by
(3) reacting a compound represented by a Formula:
A6xe2x80x94X6xe2x80x94SO2xe2x80x94NHZ6
or a salt thereof
(wherein, each symbol has the same meaning as described in [15] above to react with a compound or a salt thereof represented by Formula Lxe2x80x2xe2x80x94B6 (wherein Lxe2x80x2 is a leaving group, and the other symbol has the same meaning as defined in [15] above, respectively),or
(4) nitrating a compound represented by a Formula: 
or a salt thereof
(wherein, B7 is a phenyl group which is substituted with a substituent or substituents selected from halogen, nitro and cyano, provided that both 2- and 6-positions are not substituted at the same time).
The compound (I0), belonging to sulfonamide derivatives, may have optical isomers, diastereomers and/or any geometrical isomers thereof, and the present invention contains all the isomers and mixtures of them.
As the aryl group in the xe2x80x9caryl group which may be substitutedxe2x80x9d regarding A0, there can be mentioned C6-14 aryl groups such as phenyl, naphthyl (for example, 1-naphthyl, 2-naphthyl) and so on.
As the substituents on the said aryl groups, there can be mentioned (i) C1-4 alkyl groups (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl) optionally substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino (for example, methoxyimino, ethoxyimino), hydrazono, mono- or di-C1-4 alkylhydrazono (for example, methylhydrazono, ethylhydrazono, dimethylhydrazono) and C1-4 alkylthio (for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, isobutylthio, tert-butylthio), (ii) C3-6 cycloalkyl groups (for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl) which may be substituted with 1 to 5 halogens, (iii) C2-4 alkenyl groups (for example, vinyl, allyl, propenyl, isopropenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl) which may be substituted with 1 to 5 substituents selected from halogens, cyano and nitro, (iv) C3-6 cycloalkenyl groups (for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl) which may be substituted with 1 to 5 halogens, (v) C2-4 alkynyl groups (for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl) which may be substituted with 1 to 5 halogens, (vi) a hydroxy group, (vii) C1-4 alkoxy groups (for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy) which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy (for example, methoxy and ethoxy), (viii) formyloxy group, (ix) C1-4 alkyl-carbonyloxy group (for example, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy) which may be substituted with 1 to 5 halogens, (x) C1-4 alkoxy-carbonyloxy group (for example, methoxycarbonyloxy,ethoxycarbonyloxy, n-propoxycarbonyloxy,isopropoxycarbonyloxy) which may be substituted with 1 to 5 halogens, (xi) a mercapto group, (xii) C1-4 alkylthio groups (for example methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio) which may be substituted with 1 to 5 halogens, (xiii) C1-4 alkyl-carbonylthio groups (for example, acetylthio, propionylthio, butyrylthio, isobutyrylthio) which may be substituted with 1 to 5 halogens, (xiv) C1-4 alkoxy-carbonylthio groups (for example, methoxycarbonylthio, ethoxycarbonylthio, n-propoxycarbonylthio, isopropoxycarbonylthio) which may be substituted with 1 to 5 halogens, (xv) C1-4 alkylsulfinyl groups (for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl) which may be substituted with 1 to 5 halogens, (xvi) C1-4 alkylsulfonyl groups (for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl) which may be substituted with 1 to 5 halogens, (xvii) a sulfamoyl group, (xviii) mono- or di-C1-4 alkylsulfamoyl groups (for example, methylsulfamoyl, ethylsulfamoyl, n-propylsulfamoyl, dimethylsulfamoyl, ethylmethylsulfamoyl, diethylsulfamoyl), (xix) groups represented by 
[wherein ring C is a three- to six-membered heterocyclic group containing nitrogen (for example, aziridino, azetidino, pyrrolidino, piperidino, morpholino, thiomorpholino)], (xx) an amino group which may be substituted with 1 or 2 substituents selected from C1-4 alkyl(for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl), C2-4 alkenyl (for example, vinyl, allyl, propenyl, isopropenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl), C2-4 alkynyl (for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl), hydroxy, C1-4 alkoxy (for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy),formyloxy and C1-4 alkyl-carbonyloxy (for example, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy), formyl and C1-4 alkyl-carbonyl(for example, acetyl, propionyl, butyryl, isobutyryl), (xxi) three- to six-membered cyclic amino groups (for example, azilidino, azetidino, pyrrolidino, piperidino, morpholino, thiomorpholino), (xxii) formyl group, (xxiii) C1-4 alkyl-carbonyl groups (for example, acetyl, propionyl, butyryl, isobutyryl) which may be substituted with 1 to 5 halogens, (xxiv) C1-4 alkoxy-carbonyl groups (for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl) which may be substituted with 1 to 5 halogens, (xxv) C1-4 alkylthio-carbonyl groups (for example, (methylthio)carbonyl, (ethylthio)carbonyl, (n-propylthio)carbonyl, (isopropylthio)carbonyl, (n-butylthio)carbonyl, (isobutylthio)carbonyl, (sec-butylthio)carbonyl, (tert-butylthio)carbonyl, (xxvi) C1-4 alkoxy-thiocarbonyl groups (for example, (methoxy)thiocarbonyl, (ethoxy)thiocarbonyl, (n-propoxy)thiocarbonyl, (isopropoxy)thiocarbonyl), (xxvii) C1-4 alkylthio-thiocarbonyl groups (for example, (methylthio)thiocarbonyl, (ethylthio)thiocarbonyl, (n-propylthio)thiocarbonyl, (isopropylthio)thiocarbonyl, (n-butylthio)thiocarbonyl, (isobutylthio)thiocarbonyl, (sec-butylthio)thiocarbonyl, (tert-butylthio)thiocarbonyl), (xxviii) a carbamoyl group, (xxix) mono- or di-C1-4 alkylcarbamoyl groups (for example, methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, dimethylcarbamoyl, ethylmethylcarbamoyl, diethylcarbamoyl), (xxx) groups represented by 
(wherein ring C is a three- to six-membered heterocyclic group containing nitrogen (for example, aziridino, azetidino, pyrrolidino, piperidino, morpholino, thiomorpholino)), (xxxi) a thiocarbamoyl group, (xxxii) mono- or di-C1-4 alkyl-thiocarbamoyl groups (for example, (methyl) thiocarbamoyl, (ethyl) thiocarbamoyl, (n-propyl)thiocarbamoyl, (dimethyl)thiocarbamoyl, (ethylmethyl)thiocarbamoyl, (diethyl)thiocarbamoyl), (xxxiii)groups represented by 
(wherein ring C is a three- to six-membered heterocyclic group containing nitrogen (for example, aziridino, azetidino, pyrrolidino, piperidino, morpholino, thiomorpholino)), (xxxiv) halogen atoms (for example, fluorine, chlorine, bromine, iodine), (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group, (xliv) azoxycyano (xe2x80x94NOxe2x95x90Nxe2x80x94CN)group, and (xlv) sulfo group.
Hereinafter, the group of the above-mentioned substituents from (i) to (xlv) may be in some cases described as the substituent group (T), and the group of the above-mentioned substituents consists of those from (i) to (xliii) and (xlv)may be in some cases described as the substituent group (Txe2x80x2). (In the description of the substituents above, xe2x80x9chalogensxe2x80x9d mean fluorine, chlorine, bromine, and iodine.)
The number of substituents in the aryl group mentioned above is from one to five (more preferably from one to three). As the heterocyclic group of the xe2x80x9cheterocyclic group which may be substitutedxe2x80x9d regarding A0, there can be mentioned, for example, a five- to six-membered heterocyclic group which contains 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur atoms, or a condensed heterocyclic group composed either of five- to six-membered heterocyclic groups which contain 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur atoms and benzene rings, or of a five- to six-membered heterocyclic groups which contain 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur atoms and, the same or different, another five- to six-membered heterocyclic groups which contain 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur atoms.
As specific examples of such heterocycles, there can be mentioned pyrrolyl (for example, 1-, 2- or 3-pyrrolyl), pyrazolyl (for example, 1-, 3-, 4- or 5-pyrazolyl), imidazolyl (for example, 1-, 2-, 4-, or 5-imidazolyl), triazolyl(for example, 1,2,3-triazol-1-, 4- or 5-yl, 1,2,4-triazol-1-, 3-, 4-, or 5-yl),tetrazolyl (for example, tetrazol-1-, 2- or 5-yl), furyl (for example, 2- or 3-furyl),thienyl (for example, 2- or 3-thienyl), oxazolyl (for example, 2-, 4- or, 5-oxazolyl), isooxazolyl (for example, 3-, 4- or 5-isooxazolyl), oxadiazolyl (for example, 1,2,3-oxadiazol-4-or 5-yl, 1,2,4-oxadiazol-3- or 5-yl, 1,2,5-oxadiazol-3-yl, 1,3,4-oxadiazol-2-yl), thiazolyl (for example, 2-, 4- or 5-thiazolyl), isothiazolyl(for example, 3-, 4- or 5-isothiazolyl), thiadiazolyl (for example, 1,2,3-thiadiazol-4- or 5-yl, 1,2,4-thiadiazol-3- or 5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-thiadiazol-2-yl), pyrrolidinyl (for example, 1-, 2- or 3-pyrrolidinyl), pyridyl (for example, 2-, 3- or 4-pyridyl), pyridazinyl (for example, 3- or 4-pyridazinyl), pyrimidinyl (for example, 2-, 4- or 5-pyrimidinyl), pyrazinyl, piperidinyl (for example, 1-, 2-, 3- or 4-piperidinyl), piperazinyl (for example, 1- or 2-piperazinyl), indolyl (for example, 3H-indol-2-, 3-, 4-, 5-, 6- or 7-yl), pyranyl (for example, 2-, 3- or 4-pyranyl), thiopyranyl (for example, 2-, 3- or 4- thiopyranyl), morpholinyl(for example, 2-, 3- or 4-morpholinyl), thiomorpholinyl, quinolyl (for example, 2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl), isoquinolyl, pyrido[2,3-d]pyrimidinyl (for example, pyrido[2,3-d]pyrimidin-2-yl), naphthyridinyl such as 1,5-, 1,6-, 1,7-, 1,8-, 2,6- or 2,7-naphthyridinyl (for example, 1,5-naphthyridin-2- or 3-yl), thieno[2,3-d]pyridyl (for example, thieno[2,3-d]pyridin-3-yl), pyrazinoquinolyl (for example, pyrazino[2,3-d]quinolin-2-yl), chromenyl (for example, 2H-chromen-2-. 3-, 4-, 5- or 6-yl), chromanyl (for example, 1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-chromanyl), isochromanyl (for example, 1-, 3-, 4-, 5-, 6-, 7- or 8-isochromanyl), benzofuryl (for example, 2-, 3-, 4-, 5-, 6- or 7-benzofuryl), benzothienyl (for example, 2-, 3-, 4-, 5-, 6-, or 7-benzothienyl), benzoimidazolyl (for example, 2-, 4-, 5-, 6- or 7-benzimidazolyl), indazolyl (for example, 1H-indazol-1-, 3-, 4-, 5-, 6- or 7-yl), benzooxazolyl (for example, 2-, 4-, 5-, 6- or 7-benzooxazolyl), benzoisooxazolyl (for example, 3-, 4-, 5-, 6-or 7-benzoisooxazolyl), benzothiazolyl (for example, 2-, 4-, 5-, 6- or 7-benzothiazolyl), benzothiadiazolyl (for example, benzo-1,2,3-thiadiazol-4-, 5-, 6- or 7-yl, benzo-1,2,4-thiadiazol-3-, 4-, 5-, 6- or 7-yl, benzo-1,2,5-thiadiazol-3-, 4-, 5-, 6- or 7-yl, benzo-1,3,4-thiadiazol-2-, 4-, 5-, 6- or 7-yl), benzoisothiazolyl (for example, 3-, 4-, 5-, 6- or 7-benzzoisothiazolyl), benzotriazolyl (for example, 4-, 5-, 6-, 7- or 8-benzo-1,2,3-triazolyl, 3-, 5-, 6-, 7- or 8-benzo-1,2,4-triazolyl), cinnolyl(for example, 3-, 4-, 5-, 6-, 7-or 8-cinnolyl), phthalazinyl (for example, 1-, 5- or 6-phthalazinyl), quinazolinyl (for example, 2-, 4-, 5-, 6-, 7- or 8-quinazolinyl), quinoxalinyl (for example, 2-, 5- or 6-quinoxalinyl), imidazopyridyl (for example, imidazo[1,2-a]pyridyl such as imidazo[1,2-a]pyridin-2-yl and imidazo[1,2-a]pyridin-3-yl), imidazothiazolyl (for example, imidazo[2,1-b]thiazolyl such as imidazo[2,1-b]thiazol-5-yl), dioxaindanyl (for example, 1,3-dioxaindanyl such as 1,3-dioxaindan-2-, 4-, 5-, 6- or 7-yl).
Among these heterocyclic groups, isoxazolyl, triazolyl, pyridyl, quinolyl, thienyl, isoxazolyl, pyrazolyl, imidazolyl, benzothiadiazolyl, imidazopyridyl, imidazothiazolyl are especially preferable.
As the substituents on the said heterocyclic groups, those which are in the substituent group (T) are preferable. The number of the said substituents is 1 to 5 (preferably 1 to 3).
As preferable substituents on the aryl group in the xe2x80x9caryl group which may be substitutedxe2x80x9d or on the heterocyclic group in the xe2x80x9cheterocyclic group which may be substitutedxe2x80x9d, both represented as A0, there can be mentioned:
C1-4 alkyl which may be substituted with 1 to 5 halogens,
amino which may be substituted with one or two C1-4 alkyl-carbonyl,
(3) nitro,
(4) C1-4 alkoxy which may be substituted with 1 to 5 halogens,
(5) halogens,
(6) C1-4 alkoxy-carbonyl,
(7) cyano,
(8) mono- or di-C1-4 alkylcarbamoyl,
(9) C1-4 alkylsulfonyl,
(10) carbamoyl, and carboxyl.
As A0 phenyl groups which may be substituted with 1 to 3 substituents selected from C1-4 alkyl, halogens and cyano are preferable, and phenyl groups which may be substituted with 1 to 3 substituents selected from C1-4 alkyl and halogens are more preferable. The substituent can, most preferably, be at the 4-position of the phenyl group.
As the preferable substituents on the methylene group regarding X0, there may be mentioned:
C1-4 alkyl (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl), C1-4 alkoxy (for example,methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy), C1-4 alkylthio (for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio),
(4) halogen atoms (for example, fluorine, chlorine, bromine, iodine) and,
(5) cyano.
The number of the substituents is preferably one or two. As the substituents on the vinylene group regarding X0, there can be mentioned such substituents similar to those mentioned as the substituents on the methylene group regarding X0. The number of the said substituent is preferably one or two.
As X0, preferable are a chemical bond (a single bond or a bond), a methylene group which may be substituted with one or two C1-4 alkyl or a vinylene group which may be substituted with one or two C1-4 alkyl, a chemical bond being especially preferable.
As the xe2x80x9cheterocyclic group which may be substitutedxe2x80x9d in B0 there can be mentioned those heterocyclic groups similar to those described as the xe2x80x9cheterocyclic group which may be substitutedxe2x80x9d in A0.
The preferable heterocyclic groups is thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, imidazopyridyl, dioxaindanyl. Prefered substituents on the said heterocyclic group are nitro, halogens, cyano, C1-4 alkyl which may be substituted with 1 to 5 halogens, C1-4 alkoxy, and C1-4 alkylthio.
As the xe2x80x9caryl group which may be substitutedxe2x80x9d in B0, there can be mentioned those aryl groups similar to those described as the xe2x80x9caryl group which may be substitutedxe2x80x9d in A0. As aryl group, phenyl group is especially preferable. As preferable substituents on the said aryl group, there can be mentioned (1) halogens, (2) C1-4 alkyl which may be substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (3) C2-4 alkynyl, (4) alkoxy which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy, (5) C1-4 alkylthio, (6) C1-4 alkylsulfinyl, (7) C1-4 alkylsulfonyl, (8) C1-4 alkyl-carbonyloxy, (9) C1-4 alkoxy-carbonyl, (10) carboxyl, (11) cyano, (12) nitro, (13) nitroso, (14) formyl, (15) carbamoyl, (16) mono- or di-C1-4 alkylcarbamoyl, (17) thiocarbamoyl, (18) hydroxy, (19) mono- or di-C1-4 alkylsulfamoyl, (20) thiocyanato, (21) azoxycyano, (22) amino.
As the hydrocarbon group in the xe2x80x9chydrocarbon group which may be substitutedxe2x80x9d in Z0, there may be mentioned:
(i) a C1-6 alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl), (ii) a C2-6 alkenyl group (for example, a straight-chain C2-6 alkenyl group such as vinyl, allyl, propenyl, isopropenyl, 1-butenyl, 2-butenyl or 3-butenyl; a branched C2-6 alkenyl group such as 2-methyl-propenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 1-methyl-2-butenyl, 3-methyl-2-butenyl, 2-methyl-2-butenyl, 1-methyl-3-butenyl, 1-ethyl-2-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 2-methyl-1-pentenyl 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-3-pentenyl, 1,1-dimethyl-2-butenyl, 1,2-dimethyl-2-butenyl, 1,3-dimethyl-2-butenyl, 2,3-dimethyl-2-butenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-3-butenyl, 1-methyl-4-pentenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 1-ethyl-1-butenyl, and 1-ethyl-2-butenyl), (iii) a C2-6 alkynyl group (for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl), (iv) a C3-6 cycloalkyl group (for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl), (v) a C3-6 alkadienyl group (for example, 1,2-propadienyl, 1,2-butadienyl, 1,3-butadienyl, 3-methyl-1,2-butadienyl, 1,2-pentadienyl, 2,4-pentadienyl, 1-methyl-1,2-pentadienyl, 1-methyl-1,3-pentadienyl), and (vi) C6-14 aryl group (for example, phenyl, and naphthyl such as 1-naphthyl, 2-naphthyl).
In cases where the said hydrocarbon group is alkyl group, alkynyl group or alkadienyl group, as preferred substituents of the said hydrocarbon group, there can be mentioned (a) halogen atoms (for example, fluorine, chlorine, bromine, iodine), (b) an amino group, (c) a mono- or di-C1-4 alkylamino group (for example, methylamino, ethylamino, dimethylamino, methylethylamino), (d) a hydroxyl group, (e) a C1-4 alkoxy group (for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy) which may be substituted with 1 to 5 (more preferably 1 to 3) halogens (for example, fluorine, chlorine,bromine, iodine), (f) mercapto, (g) C1-4 alkylthio (for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio), (h) C1-4 alkylsulfinyl (for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl), (i) C1-4 alkylsulfonyl (for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl), (j) cyano, (k) C1-4 alkoxy-carbonyl (for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl), (l) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl (for example, methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, dimethylcarbamoyl, ethylmethylcarbamoyl, diethylcarbamoyl).
The number of the said substituents is 1 to 5 (more preferably 1 to 3).
In cases where the said hydrocarbon group is a cycloalkyl group or an aryl group, as the substituents on the said hydrocarbon group, there can be mentioned a C1-4 alkyl group which may be substituted with 1 to 5 halogens (for example, fluorine, chlorine, bromine, iodine) atoms (for example, methyl, ethyl, propyl, isopropyl, tert-butyl, chloromethyl, trifluoromethyl), (b) halogen atoms (for example, fluorine, chlorine, bromine, iodine) (c) an amino group, (d) a mono- or di-C1-4 alkylamino group (for example, methylamino, ethylamino, dimethylamino, methylethylamino), (e) a hydroxyl group, (f) a C1-4 alkoxy (for example, fluorine, chlorine, bromine, iodine) (for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy) which may be substituted with 1 to 5 (more preferably 1 to 3) halogens, (g) mercapto, (h) C14 alkylthio (for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio), (i) C1-4 alkylsulfinyl (for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl), (j) C1-4 alkylsulfonyl (for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl), (k) cyano, (1) C1-4 alkoxy-carbonyl (for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl), (m) carbamoyl and (n) mono- or di-C1-4 alkyl-carbamoyl (for example, methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, dimethylcarbamoyl, ethylmethylcarbamoyl, diethylcarbamoyl).
The number of the said substituents is 1 to 5 (more preferably 1 to 3).
As the xe2x80x9cacyl groupxe2x80x9d in xe2x80x9can acyl group which may be substitutedxe2x80x9d in Z0, there may be mentioned (i) a C1-4 alkyl-carbonyl group (for example, acetyl, propionyl, butyryl, isobutyryl), (ii) a C1-4 alkoxy-carbonyl group (for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl), (iii) a C1-4 alkylthio-carbonyl group (for example, (methylthio)carbonyl, (ethylthio)carbonyl, (n-propylthio)carbonyl, (isopropylthio)carbonyl, (n-butylthio)carbonyl, (isobutylthio)carbonyl, (sec-butylthio)carbonyl, (tert-butylthio)carbonyl), (iv) a C1-4 alkoxy-thiocarbonyl group (for example, (methoxy)thiocarbonyl, (ethoxy)thiocarbonyl, (n-propoxy)thiocarbonyl, (isopropoxy)thiocarbonyl), (v) a C1-4 alkylthio-thiocarbonyl (for example, (methylthio)thiocarbonyl, (ethylthio)thiocarbonyl, (n-propylthio)thiocarbonyl, (isopropylthio)thiocarbonyl, (n-butylthio)thiocarbonyl, (isobutylthio)thiocarbonyl, (sec-butylthio)thiocarbonyl, (tert-butylthio)thiocarbonyl), (vi) a mono- or di-C1-4 alkyl-carbamoyl group (for example, methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, dimethylcarbamoyl, ethylmethylcarbamoyl, diethylcarbamoyl), and (vii) a mono- or di-C1-4 alkyl-thiocarbamoyl group (for example, (methyl)thiocarbamoyl, (ethyl)thiocarbamoyl, (n-propyl)thiocarbamoyl, (dimethyl)thiocarbamoyl, (ethylmethyl)thiocarbamoyl, (diethyl)thiocarbamoyl). As the substituents on the said acyl group, halogens (for example, fluorine, chlorine, bromine, iodine) are preferable. The number of the said substituents is 1 to 5 (more preferably 1 to 3).
As the substituents on the xe2x80x9camino group which may be substitutedxe2x80x9d in Z0, there may be mentioned
C1-4 alkyl (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl),
C1-4 alkyl-carbonyl (for example, acetyl, propionyl, butyryl, isobutyryl) which may be substituted with 1 to 5 (more preferably 1 to 3) halogens (for example, fluorine, chlorine, bromine, iodine),
C1-4 alkoxy-carbonyl (for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl),
mono- or di-C1-4 alkyl-carbamoyl (for example, methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, dimethylcarbamoyl, ethylmethylcarbamoyl, diethylcarbamoyl), and (e) mono- or di-C1-4 alkyl-thiocarbamoyl (for example, (methyl)thiocarbamoyl, (ethyl)thiocarbamoyl, (n-propyl)thiocarbamoyl, (dimethyl)thiocarbamoyl, (ethylmethyl)thiocarbamoyl, (diethyl)thiocarbamoyl).
The number of the said substituents is preferably 1 or 2.
As the xe2x80x9chydrocarbon groups which may be substitutedxe2x80x9d in R1, R2, R3 and R4, there may be mentioned those groups similar to those mentioned as the xe2x80x9chydrocarbon groups which may be substitutedxe2x80x9d in Z0.
Among the xe2x80x9chydrocarbon groups which may be substitutedxe2x80x9d in R1 and R2, C1-4 alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl) are more preferable. Among the xe2x80x9chydrocarbon groups which may be substitutedxe2x80x9d in R3, C1-4 alkyl groups (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl) which may be substituted with 1 to 5 (more preferably 1 to 3) halogens (fluorine, chlorine, bromine, iodine) are preferable.
Among the xe2x80x9chydrocarbon groups which may be substitutedxe2x80x9d in R4, (1) C1-4 alkyl groups (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl) which may be substituted with 1 to 5 (more preferably 1 to 3) halogens (fluorine, chlorine, bromine, iodine), and (2) C6-14 aryl groups (for example, phenyl and naphthyl such as 1-naphthyl and 2-naphthyl) which may be substituted with 1 to 5 (more preferably 1 to 3) C1-4 alkyl (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl) are preferable.
As the cyclic amino groups in Z0, there may be mentioned three- to six-membered cyclic amino groups (for example, aziridino, azetidino, pyrrolidino, piperidino, morpholino, thiomorpholino).
As the xe2x80x9cacyl group which may be substitutedxe2x80x9d in R3, there may be mentioned those groups similar to those mentioned above regarding the xe2x80x9cacyl group which may be substitutedxe2x80x9d in Z0. Among them, C1-4 alkyl-carbonyl groups (for example, acetyl, propionyl, butyryl, isobutyryl) which may be substituted with 1 to 5 (more preferably 1 to 3) halogens (for example, fluorine, chlorine, bromine, iodine), and C1-4 alkoxy-carbonyl groups (for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl) which may be substituted with 1 to 5 (more preferably 1 to 3)halogens (for example, fluorine, chlorine, bromine, iodine) are more preferable.
As the xe2x80x9calkylsulfonylxe2x80x9d in the xe2x80x9calkylsulfonyl groups which may be substitutedxe2x80x9d in R3 there may be mentioned C1-4 alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, and so on. As the substituents on the said alkylsulfonyl groups, halogens (for example, fluorine, chlorine, bromine, iodine) are preferable. The number of the said substituents is 1 to 5 (more preferably 1 to 3).
Z0 is more preferably, among those mentioned above,
C1-6 alkyl group which may be substituted with 1 to 3 substituents selected from hydroxy, halogens, cyano, C1-4 alkylthio, C1-4 alkoxy, C1-4 alkoxy-carbonyl and mono- or di-C1-4 alkylamino,
(2) C2-6 alkenyl group,
(3) C2-6 alkynyl group which may be substituted with 1 to 3 halogens,
(4) C3-6 cycloalkyl group,
(5) C3-6 alkadienyl group,
(6) phenyl group,
(7) C1-4 alkyl-carbonyl group which may be substituted with 1 to 3 halogens,
(8) amino group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkyl-carbonyl and C1-4 alkoxy-carbonyl,
(9) a group represented by xe2x80x94Nxe2x95x90CR1R2 (where R1 and R2 are the same or different, and are a hydrogen atom or a C1-4 alkyl group),
(10) C1-4 alkoxy group,
(11) C1-4 alkyl-carbonyloxy group,
(12) C1-4 alkylthio group which may be substituted with 1 to 5 halogens,
(13) C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens,
(14) C1-4 alkylsulfonyl group,
(15) phenylsulfonyl group which may be substituted with 1 to 3 C1-4 alkyl.
As the salt of compound (I0), there may be mentioned any salts which are acceptable agrochemically. In the cases where the compound (I0) is of basic nature, there may be mentioned salts with inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid, and perchloric acid, and those with organic acids such as formic acid, acetic acid, propionic acid, tartaric acid, malic acid, citric acid, oxalic acid, succinic acid, benzoic acid, picric acid, methanesulfonic acid, p-toluenesulfonic acid and so on. In the cases where the compound (I0) is of acidic nature, there may be mentioned salts, alkali metals such as lithium, sodium, potassium and so on, salts with alkaline earth metals such as magnesium, calcium and so on, ammonium salts such as ammonia, methylamine, dimethylamine, trimethylamine, triethylamine, ethylenediamine, TMEDA (tetramethylethylenediamine), aniline, N,N-dimethylaniline,pyridine, lutidine,collidine, hydrazine, and so on, and salts with, for example, urea and guanidine, and so on.
Among compound (I0) or salts thereof, those represented by compound (I), compound (II), compound (III), compound (IV) and compound (V) or salts thereof are more preferable.
[1] Compound (I) or salts thereof are those compounds represented by the Formula (I) or salts thereof, 
[wherein, A1 is (1) an aryl group which may be substituted, or (2) a heterocyclic group which may be substituted,
X1 is (1) a chemical bond, (2) a methylene group which may be substituted, (3) a vinylene group which may be substituted,
B1 is a 5 membered heterocyclic group which may be substituted (except for an isoxazolyl group) or a condensed heterocyclic group which may be substituted,
Z1 is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein R1 and R2 are the same or different, and are a hydrogen atom or a hydrocarbon group which may be substituted, (6) a cyclic amino group, (7) a group represented by xe2x80x94OR3 (wherein R3 is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or an alkylsulfonylgroup which may be substituted, or (8) a group represented by xe2x80x94S(O)nR4 (wherein n is an integer from 0 to 2, R4 a hydrogen atom or hydrocarbon group which may be substituted).
As the substituents on A1, X1 and Z1, there may be mentioned those on A0, X0 and Z0, mentioned above.
As the five-membered heterocylic group in the xe2x80x9cfive-membered heterocyclic group which may be substitutedxe2x80x9d in B1, there may be mentioned, a five-membered heterocyclic group, for example, those heterocyclic groups which contain, nitrogen and/or sulfur atoms as the ring constructing atoms besides carbon atoms,and especially those which contain 1 to 4 (more preferably 1 to 3) heteroatoms selected from nitrogen and sulfur atoms, exemplified by pyrolyl (for example, 1-, 2- or 3-pyrolyl), pyrazolyl (for example 1-. 3-, 4- or 5-pyrazolyl), imidazolyl (for example, 1-, 2-, 4- or 5-imidazolyl), triazolyl (for example, 1,2,3-triazol-1-, 4- or 5-yl, 1,2,4-triazol-1-, 3-, 4- or 5-yl), tetrazolyl (for example, tetrazol-1-, 2- or 5-yl), thienyl (for example, 2- or 3-thienyl), thiazolyl (for example, 2-, 4- or 5-thiazolyl), isothiazolyl (for example, 3-, 4- or 5-isothiazolyl), thiadiazolyl (for example, 1,2,3-thiadiazol-4- or 5-yl, 1,2,4-thiadiazol-3- or 5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-thiadiazol-2-yl), pyrrolidinyl (for example, 1-, 2- or 3-pyrrolidinyl), and so on.
Especially preferable are thienyl, pyrazolyl, isothiazolyl, imidazolyl, thiazolyl and thiadiazolyl.
As the substituents on the said five-membered heterocyclic groups, those selected from the group of substituents (T) described above are preferable. The number of the substituents is 1 to 5 (more preferably 1 to 3). The most preferable substituents are halogens, nitro, cyano, and C1-4 alkyl, C1-4 alkoxy, and C1-4 alkylthio substituted with 1 to 5 (more preferably 1 to 3) halogens.
As the xe2x80x9ccondensed heterocyclic groupsxe2x80x9d in the xe2x80x9ccondensed heterocyclic groups which may be substitutedxe2x80x9d in B1, those condensed heterocyclic groups which are composed of five- to six-membered heterocycles and benzene rings or five- to six-membered heterocycles and five- to six-membered heterocycles are preferable.
As specific examples of such preferable condensed heterocycles, there can be mentioned indolyl (for example, 3H-indol-2-, 3-, 4-, 5-, 6- or 7-yl), quinolyl (for example, 2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl), isoquinolyl, pyrido[2,3-d]pyrimidinyl (for example, pyrido[2,3-d]pyrimidin-2-yl), naphthyridinyl such as 1,5-, 1,6-, 1,7-, 1,8-, 2,6- or 2,7-naphthyridinyl (for example, 1,5-naphthyridin-2- or 3-yl), thieno[2,3-d]pyridyl (for example, thieno[2,3-d]pyridin-2-yl), pyrazinoquinolyl (for example, pyrazino[2,3-d]quinolin-2-yl), chromenyl (for example, 2H-chromen-2-, 3-, 4-, 5- or 6-yl), chromanyl (for example, 1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-chromanyl), isochromanyl (for example, 2-, 3-, 4- ,5-, 6-, 7- or 8-isochromanyl), benzofuryl (for example, 2-, 3-, 4-, 5-, 6- or 7-benzofuryl), benzothienyl (for example, 2-, 3-, 4-, 5-, 6- or 7-benzothienyl), benzoimidazolyl (for example, 2-, 4-, 5-, 6- or 7-benzimidazolyl), indazolyl (for example, 1H-indazol-1-, 3-, 4-, 5-, 6- or 7-yl), benzooxazolyl (for example, 2-, 4-, 5-, 6- or 7-benzooxazolyl), benzoisooxazolyl (for example, 3-, 4-, 5-, 6- or 7-benzoisooxazolyl), benzothiazolyl (for example, 2-, 4-, 5-, 6- or 7-benzothiazolyl), benzothiadiazolyl (for example, benzo-1,2,3-thiadiazol-4-, 5-, 6- or 7-yl, benzo-1,2,4-thiadiazol-3-, 4-, 5-, 6- or 7-yl), benzo-1,2,5-thiadiazol-3-, 4-, 5-, 6- or 7-yl, benzo-1,3,4-thiadiazol-2-, 4-, 5-, 6- or 7-yl), benzoisothiazolyl (for example, 3-, 4-, 5-,6- or 7-benzoisothiazolyl), benzotriazolyl (for example, 4-, 5-, 6-, 7- or 8-benzo-1,2,3-triazolyl, 3-, 5-, 6-, 7- or 8-benzo-1,2,4-triazolyl), cinnolyl (for example, 3-, 4-, 5-, 6-, 7- or 8-cinnolyl), phthalazinyl (for example, 1-, 5- or 6-phthalazinyl), quinazolynyl (for example, 2-, 4-, 5-, 6-, 7- or 8-quinazolynyl), quinoxalinyl (for example, 2-, 5- or 6-quinoxalinyl), imidazopyridyl (for example, imidazo[1,2-a]pyridyl such as imidazo[1,2-a]pyridin-2-yl, imidazo[1,2-a]pyridin-3-yl, and so on) imidazothiazolyl (for example, imidazo[2,1-b]thiazolyl such as imidazo[2,1-b]thiazol-5-yl), dioxaindanyl (for example, 1,3-dioxaindanyl such as 1,3-dioxaindan-2-, 4-, 5-, 6- or 7-yl, and so on). Among these, imidazopyridyl and dioxaindanyl are more preferable.
As the substituents on the xe2x80x9ccondensed heterocyclic groupsxe2x80x9d,those selected from the group of substituents (T) described above are preferable. The number of the substituents is 1 to 5 (more preferably 1 to 3). Among those substituents, nitro is especially preferable.
Among compounds included in compound (I), preferable are the compounds represented by the Formula (I) above or salts thereof. In the Formula(I), A1 is a C6-14 aryl group which may be substituted with 1 to 3 C1-4 alkyl groups,
X1 is a chemical bond, B1 is a thienyl group, pyrazolyl group, isothiazolyl group, imidazolyl group, thiazolyl group, thiadiazolyl group, dioxaindanyl group or imidazopyridyl group, each of which may be substituted with 1 to 5 substituents selected from C1-4 alkyl which may be substituted with 1 to 5 halogens, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, cyano, halogens and nitro, Z1 is a C1-6 alkyl group or C1-4 alkoxy group.
Hereinafter, the more preferable embodiments of the compound (I) and the salts thereof are described:
As A1, a phenyl which may be substituted with 1 to 3 C1-4 alkyl is preferable, and the 4-methylphenyl group is especially preferable.
(2) As B1, either (i) a thienyl group, a pyrazolyl group, an isothiazolyl group, an imidazolyl group, a thiazolyl group or a thiadiazolyl group, each of which may be substituted with 1 to 5 substitutents selected from C1-4 alkyl substituted with 1 to 5 halogens, C1-4 alkoxy, C1-4 alkylthio, cyano, halogens and nitro, or (ii) a dioxaindanyl group or an imidazopyridyl group which may be substituted with 1 to 3 nitros are preferable.
The more preferable B1 are:
(i) the thienyl group which may be substituted with 1 to 3 substituents selected from halogens and nitro, (ii) the pyrazolyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl, nitro and cyano, (iii) the imidazolyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl and nitro, (iv) the thiazolyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl which may be substituted with 1 to 5 halogens, C1-4 alkylthio, halogens, nitro and cyano, (v) the thiadiazolyl group (more preferably a 1,3,4-thiadiazolyl group) which may be substituted with C1-4 alkyl which may be substituted with 1 to 5 halogens, (vi) the isothiazolyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl which may be substituted with 1 to 5 halogens, C1-4 alkoxy, nitro and cyano, (vii) the 1,3-dioxaindanyl group which may be substituted with 1 to 3 nitro, and (viii) the imidazo[1,2-a]pyridyl group which may be substituted with 1 to 3 nitro,
(3) As Z1, a C1-6 alkyl group or a C1-4 alkoxy group is preferable.
(4) As X1, a chemical bond (a single bond or a bond) is preferable.
The preferable embodiments regarding A1, B1, Z1 and X1 described in (1) to (4) above can be combined together arbitrarily.
[2] Compound (II) or salts thereof are the compounds represented by the Formula (II) 
or salts thereof,
[where A2 is (1) an aryl group or a heterocyclic group or (2) heterocyclic group, which may be substituted with 1 to 5 (more preferably 1 to 3) substituents selected from the substituent group (Txe2x80x2) described above,
X2 (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted,
B2 is an aryl group which may be substituted,
Z2 is (1) an alkyl group which may be substituted with substituents selected from mono- or di-C1-6 alkylamino, hydroxy, halogens, C1-6 alkoxy, C1-6 alkoxy-carbonyl, C1-6 alkylthio and cyano, (2) the vinyl group, (3) the allyl group, (4) the propadienyl group, (5) the alkynyl group which may be substituted, (6) the cycloalkyl group which may be substituted, (7) the aryl group which may be substituted, (8) the acyl group which may be substituted, (9) the formyl group, (10) the amino group which may be substituted, (11) the group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein R1 and R2 are the same or different, and are a hydrogen or a hydrocarbon group which may be substituted), (12) the cyclic amino group, (13) the group represented by xe2x80x94OR3 (wherein R3 is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group, or a alkylsulfonyl group which may be substituted), or
the group represented by xe2x80x94S(O)nR4 (where n is an integer from 0 to 2, R4 a hydrogen atom or hydrocarbon group which may be substituted).
As an aryl group in A2, there may be mentioned a C6-14 aryl groups such as phenyl, and naphthyl (for example, 1-naphthyl, 2-naphthyl).
A phenyl group is especially preferable.
As a heterocyclic group which may be substituted in A2, there may be mentioned the same heterocyclic groups as those which may be substituted in A0.
As the substituents on X2, there can be mentioned the same ones as those on X0.
As the aryl group which may be substituted in B2, there can be mentioned the same ones as those in B0. As the aryl group, a phenyl group is especially preferable.
As the alkyl group in xe2x80x9can alkyl group which may be substituted with substituents selected from mono- or di-C1-6 alkylamino, hydroxy, halogens, C1-6 alkoxy, C1-6 alkoxy-carbonyl, C1-6 alkylthio and cyanoxe2x80x9d in Z2, there may be mentioned C1-6 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl and soon. The number of substituents on the said alkyl groups is 1 to 5, or more preferably 1 to 3. As the mono- or di-C1-6 alkylamino groups as the said substituent, there may be mentioned methylamino, ethylamino, n-propylamino, dimethylamino, ethylmethylamino, diethylamino, and mono- or di-C1-4 alkylamino groups are especially preferable. As halogens, there may be mentioned fluorine, chlorine, bromine, and iodine. As C1-6 alkoxy, there may be mentioned methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and so on, the C1-4 alkoxy groups being especially preferable. As C1-6 alkoxy-carbonyl, there may be mentioned methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, and so on, the C1-4 alkoxy-carbonyl groups being especially preferable. As C1-6 alkylthio, there may be mentioned methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, and so on, the C1-4 alkylthio groups being especially preferable. As alkynyl in xe2x80x9calkynyl which may be substitutedxe2x80x9d in Z2, there may be mentioned C2-6 alkynyl group such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and so on. As cycloalkyl in xe2x80x9ccycloalkyl which may be substitutedxe2x80x9d, there may be mentioned C3-6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and so on. As aryl in xe2x80x9cthe aryl group which may be substitutedxe2x80x9d, there may be mentioned C6-14 aryl such as phenyl, naphthyl, (for example, 1-naphthyl, 2-naphthyl) and so on. As the substituents on alkynyl group, cycloalkyl group or aryl group described above, there may be mentioned the same substituents as those on alkynyl group, cycloalkyl group or aryl group exemplified in hydrocarbon group in xe2x80x9chydrocarbon group which may be substitutedxe2x80x9d regarding Z0 mentioned above, Each of xe2x80x9can acyl group which may be substitutedxe2x80x9d, xe2x80x9can amino group which may be substitutedxe2x80x9d, xe2x80x9ca group represented by xe2x80x94Nxe2x95x90CR1R2xe2x80x9d, xe2x80x9ca cyclic amino groupxe2x80x9d, xe2x80x9ca group represented by xe2x80x94OR3xe2x80x9d and xe2x80x9ca group represented by xe2x80x94S(O)nR4xe2x80x9d in Z2 has the same meaning as that of xe2x80x9can acyl group which may be substitutedxe2x80x9d, xe2x80x9can amino group which may be substitutedxe2x80x9d, xe2x80x9ca group represented by xe2x80x94Nxe2x95x90CR1R2xe2x80x9d, xe2x80x9ca cyclic amino groupxe2x80x9d, xe2x80x9ca group represented by xe2x80x94OR 3 and xe2x80x9ca group represented by xe2x80x94S(O)nR4 in Z0 mentioned above.
Among compounds included in compound (II), preferable are the compounds represented by the Formula (II) above or salts thereof.
In the Formula, [where A2 is (1) a C6-14 aryl group which may be substituted with 1 to 5 substituents selected from (i) a C1-4 alkyl group which may be substituted with 1 to 5 halogens, (ii) the C1-4 alkoxy group which may be substituted with 1 to 5 halogens, (iii) the amino group which may be substituted with 1 or 2 C1-4 alkylcarbonyl, (iv) the C1-4 alkoxy-carbonyl group, (v) halogen atoms, (vi) the cyano group, and (vii) the nitro group, or the thienyl group, the triazolyl group, the imidazolyl group, the isooxazolyl group, the pyrazolyl group, the pyridyl group, the quinolyl group, the benzothiadiazolyl group, the imidazothiazolyl group or the imidazopyridyl group, each of which may be substituted with 1 to 5-substitutents selected from (i) the C1-4 alkyl group, (ii) the C1-4 alkoxy-carbonyl group, (iii) the carbamoyl group, (iv) the mono- or di-C1-4 alkylcarbamoyl group, (v) C1-4 alkylsulfonyl group, (vi) halogen atoms, (vii) the carboxyl group and (viii) the cyano group, X2 is (1) the chemical bond, (2) the methylene group which may be substituted with 1 or 2 C1-4 alkyl, (3) the vinylene group which may be substituted with 1 or 2 C1-4 alkyl, B2 is a C6-14 aryl group which may be substituted with 1 to 5 substituents selected from (1) a C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (2) a C2-4 alkynyl group, (3) the hydroxy group, (4) the C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy groups, (5) a C1-4 alkyl-carbonyloxy group, (6) the C1-4 alkylthio group, (7) the C1-4 alkylsulfinyl group, (8) the C1-4 alkylsulfonyl group, (9) the mono or di-C1-4 alkylsulfamoyl group, (10) the amino group, (11) the formyl group, (12) the C1-4 alkoxy-carbonyl group, the carbamoyl group, the mono- or di-C1-4 alkylcarbamoyl group, the thiocarbamoyl group, halogen atoms, the carboxyl group, the thiocyanato group, the cyano group, the nitroso group, and the nitro group, Z2 is (1) the C1-6 alkyl group which may be substituted with 1 to 5 substituents selected from mono- or di-C1-4 alkylamino, hydroxy, halogens, C1-4 alkoxy, C1-4 alkoxy-carbonyl, C1-4 alkylthio and cyano, (2) the vinyl group, (3) the allyl group, (4) the propadienyl group, (5) the C2-6 alkynyl group which may be substituted with 1 to 5 halogens, (6) the C3-6 cycloalkyl group, (7) the C6-14 aryl group, (8) the C1-4 alkyl-carbonyl which may be substituted with 1 to 5 halogens, (9) the amino group which may be substituted with 1 or 2 substituents selected from C1-4 alkyl, C1-4 alkyl-carbonyl and C14 alkoxy-carbonyl, (10) the group represented by xe2x80x94Nxe2x95x90CR1R2 (where R1 and R2 are a C1-4 alkyl group, respectively), (11) the group represented by xe2x80x94OR3 (where R3 is a C1-4 alkyl group or a C1-4 alkyl-carbonyl group) or (12) the group represented by xe2x80x94S(O)nR4 (wherein, n is an integer from 0 to 2, R4 is (a) the C1-4 alkyl group which may be substituted with 1 to 5 halogens, or (b) the C6-14 aryl group which may be substituted with 1 to 5 C1-4 alkyl groups).
Hereinafter, the more preferable embodiments of the compound (II) and the salts thereof are described:
A2 is (a) the phenyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl which may be substituted with 1 to 3 halogens, halogens, nitro, cyano, acetylamino, C1-4 alkoxy which may be substituted with 1 to 3 halogens and C1-4 alkoxy-carbonyl, (b) the naphthyl group, (c) the isoxazolyl group which may be substituted with 1 to 3 C1-4 alkyl groups, (d) the triazolyl group which may be substituted with 1 to 3 mono-or di-C1-4 carbamoyl, (e) the pyridyl group, (f) the quinolyl group, (g) the thienyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl and halogens, (h) the pyrazolyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl, C1-4 alkoxy-carbonyl, carboxyl, carbamoyl, cyano and halogens, (i) the imidazolyl group which may be substituted with 1 to 3 C1-4 alkyl, (j) the benzothiadiazolyl group (preferably a 2,1,3-benzothiadiazolyl group), (k) the imidazothiazolyl group (preferably an imidazo[2,1-b]thiazolyl group) which may be substituted with 1 to 3 halogens, (1) the imidazopyridyl group (preferably an imidazo[1,2-a]pyridyl group) which may be substituted with 1 to 3 substituents selected from halogens and C1-4 alkylsufonyl. More preferable is a phenyl or a thienyl group which may be substituted with 1 to 3 substituents such as C1-4 alkyl groups, C1-4 alkoxy groups, halogens or cyano group is more preferable. Among these, a phenyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl and halogens is much more preferable. And the phenyl group which is substituted at the 4-position with a methyl group or a chlorine atom is the most preferable.
(2) As B2, preferable is a phenyl group which is substituted at the 2- or 4-position with substituent selected from (a) the C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (b) the C2-4 alkynyl group, (c) the hydroxy group, (d) the C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy, (e) a C1-4 alkyl-carbonyloxy group, (f) a C1-4 alkylthio group, (g) a C1-4 alkylsulfinyl group, (h) a C1-4 alkylsulfonyl group, (i) a mono- or di-C1-4 alkylsulfamoyl group, (j) formyl group, (k) a C1-4 alkoxy-carbonyl group, (1) a carbamoyl group, (m) a mono- or di-C1-4 alkylcarbamoyl group, (n) a thiocarbamoyl group, (o) halogen atoms, (p) a carboxyl group, (q) a thicyanato group, (r) a cyano group, s a nitroso group, and (t) a nitro group.
As B21- a group represented by 
(wherein, M1 is a nitro group, a cyano group, a trifluoromethyl group or a thiocarbamoyl group, and M2 is halogen atoms, a cyano group, a nitro group or a trifluoromethyl group) is especially preferable.
(3) As Z2, preferable are (a) a C1-6 alkyl group which may be substituted with 1 to 5 substituents selected from mono- or di-C1-4 alkylamino, hydroxy, halogens, C1-4 alkoxy, C1-4 alkoxy-carbony, C1-4 alkylthio and cyano, (b) a vinyl group, (c) an allyl group, (d) a propadienyl group, (e) a C2-6 alkynyl group which may be substituted with 1 to 5 halogens, or (f) a C3-6 cycloalkyl group, or (g) a C1-4 alkoxy group. Among these, a C1-6 alkyl group, a C3-6 cycloalkyl group, a vinyl group, an allyl group, a C2-6 alkynyl group or a C1-4 alkoxy group is especially preferable.
(4) X2 is preferably a chemical bond (a single bond or a bond).
The preferable embodiments of A2, B2, Z2 and X2 described in (1) to (4) above, can be combined arbitrarily.
Another preferable embodiments of compounds (II) or salts thereof are preferably the compounds or salts thereof described the following:
A2 is a phenyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl groups, halogens and cyano, X2 is a chemical bond, B2is a phenyl group which may be substituted with 1 to 5 substituents selected from (1) a C1-4 alkyl group which may be substituted with 1 to 3 halogens, (2) a C1-4 alkoxy group, (3) a C1-4 alkylthio group, (4) a thiocarbamoyl, (5) halogen atoms, (6) a cyano group, and (7) a nitro group, Z2 is (1) a C1-6 alkyl group which may be substituted with 1 to 3 C1-4 alkoxy, (2) a C3-6 cycloalkyl group, (3) an allyl group or (4) a C1-4 alkoxy group.
[3] Compound (III) or salts thereof are preferably the compounds represented by the Formula (III): 
or a salt thereof,
[where A3 is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X3 is (1) a chemical bond, (2) a methylene group which may be substituted or (3) a vinylene group which may be substituted, B3 is a six-membered heterocyclic group containing sucstituents, Z3 is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein, R1 and R2 are the same or different, and are a hydrogen atom or hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group represented by xe2x80x94OR3 (wherein R3 is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or a sulfonyl group which may be substituted), or (8) a group represented by xe2x80x94S(O)nR4 (wherein n is an integer from 0 to 2, R4 is a hydrogen atom or a hydrocarbon group which may be substituted)].
The substituents on A3, X3 and Z3 are the same as those on A0, X0 and Z0, respectively.
As the xe2x80x9csix-membered heterocyclic groupxe2x80x9d in the xe2x80x9csix-membered heterocyclic group with substituentsxe2x80x9d in B3, there can be mentioned six-membered heterocyclic groups comprising 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur atoms. As the specific examples, there can be mentioned pyridyl (for example, 2-, 3- or 4-pyridyl), pyridazinyl (for example, 3- or 4-pyridazinyl), pyrimidinyl (for example, 2-, 4-, or 5-pyrimidinyl), pyrazinyl, piperidinyl (for example, 1-, 2-, 3- or 4-piperidinyl), piperazinyl (for example, 1- or 2-piperazinyl), and so on. Among these six-membered heterocyclic groups, pyridyl, pyridazinyl and pyrimidinyl are especially preferable.
As substituents on the said six-membered heterocyclic groups, those included in the substituents group (T) mentioned above are preferable. The number of the said substituents is 1 to 5 (more preferably 1 to 3).
Among the compounds included in compound (III), preferable are those represented by the Formula (III)or salts thereof. In the Formula(III), wherein A3 is a phenyl group which may be substituted with 1 to 5 C1-4 alkyl or an imidazolyl group which may be substituted with one or two C1-4 alkyl, X3 is a chemical bond, B3 is a pyridyl group, a pyridazinyl group or a pyrimidinyl group which may be substituted with 1 to 5 substituents selected from C1-4 alkyl, C1-4 alkoxy, halogens and nitro, Z3 is a C1-6 alkyl group or C3-6 cycloalkyl group or salts thereof. As for A3 above, a phenyl group which may be substituted with 1 to 5 C1-4 alkyl is more preferable, and furthermore a 4-methylphenyl group is the most preferable.
[4] Compounds(IV) or salts thereof are the compounds represented by the Formula (IV): 
or salts thereof,
[wherein A4 is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X4 is (1) a chemical bond, (2) a methylene group which may be substituted or (3) a vinylene group which may be substituted, B4 is a pyridazinyl group or a pyradinyl group, Z4 is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by xe2x80x94Nxe2x95x90CR1R2 (wherein R1 and R2 are the same or different, and are a hydrogen atom or a hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group represented by xe2x80x94OR3 (wherein R3is a hydrogen atom, a hydrocarbon group which may be substituted an acyl group which may be substituted with hormyl group or sulfonyl group which may be substituted, (8) a group represented by xe2x80x94S(O)nR4 (wherein n is an integer from 0 to 2, R4 is a hydrogen atom or a hydrocarbon group which may be substituted].
Substituents on A4, X4 and Z4 are the same as those on A0, X0 and Z0 described above, respectively.
[5] Compounds (V) or salts thereof are the compounds represented by the Formula (V): 
or salts thereof,
[wherein A5 is a 4-methylphenyl group, X5 is a chemical bond (a single bond or a bond), B5 is a pyridyl group or a pyrimidinyl group, Z5 is a C1-4 alkyl group (for example, methyl, ethyl, n-propyl, isopropyl)].
Among the compound (1) to (V) stated above, compound (I) to (III) or salts thereof are more preferable, and compound (II) or salts thereof are especially preferable.
Among the compound (I0) or salts thereof, the compound (VI) shown below or salts thereof are novel compounds and can be used especially preferably. The said comound (VI) or salts thereof are compounds included in the compound (II) or salts thereof mentioned above. Compounds represented by the Formul(VI) and saltys thereof, 
[wherein, A6 is a phenyl group which may be substituted with substituents selected from C1-4 alkyl (for example, methyl, ethyl, n-propyl, isopropyl), halogens (for example, fluorine, chlorine, bromine, iodine) and cyano, X6 is a chemical bond (a single bond or a bond), B6 is a 2-nitrophenyl group (or 6-nitrophenyl group) or 2-cyanophenyl group (or 6-cyanophenyl group) which may be substituted with substituents selected from halogen atoms (for example, fluorine, chlorine, bromine, iodine), nitro and cyano, Z6 is an ethyl group, an isopropyl group, a cyclopropyl group, a methoxy group, an ethoxy group or an isopropoxy group].
Especially preferable are the compounds or salts thereof which have as A6 a phenyl group which may be substituted with substituents selected from C1-4 alkyl, halogens and cyano, as X6 a chemical bond, as B6 a 2-nitrophenyl group which may be substituted with substituents selected from halogen atoms, nitro and cyano, and as Z6 an ethyl group, an isopropyl group or a cyclopropyl group.
The number of the substituents on the phenyl group as A6 is 1 to 3. As the said substituent, methyl and chlorine atom are especially preferable. The substitutent of the said phenyl group is preferably at position 4 of the said phenyl group.
The number of substituents on the 2-nitrophenyl group (or 6-nitrophenyl group) or the 2-cyanophenyl group (or 6-cyanophenyl group) as B6 is 1 to 3. As the said substituent, halogens and cyano are especially preferable. The said substituents are preferably at the 4 position of the 2-nitrophenyl (or 6-nitrophneyl) group or 2-cyanophenyl (or 6-cyanophenyl) group.
When compound (I0), (I), (II), (III), (IV), (V) or (VI) or salts thereof mentioned above (hereinafter, they may be called as xe2x80x9ccompound (I0) or the salts thereofxe2x80x9d for short) are used as microbicidal compositions, they can be applied in the per se known forms for general use of agrochemical compositions. Namely, depending on the objects one or more than two kinds (preferably not less than one nor more than three) of compound (I0) or salts thereof are taken as the effective constituents and mixed with or dispersed in some appropriate liquid carrier, or mixed with or adsorbed on some appropriate solid carrier to get various forms of compositions, for example, emulsions, oils, aqueous suspensions, liquids, ULV preparations, hydrates, powders, DL (driftless) powders, granules, fine granules, fine granules F, flowable preparations, dry-flowable preparations, tablets, Jumbo preparations, sprays, ointments, pastes, foams, aerosols, micocapsules, seed coating agents, fumigants, and stick preparations for infusing the crops. These preparations may be further admixtured, if necessary, for example, with emulsifiers, suspending agents, spreading agents, permeating agents, moistening agents, dispersing agents, mucilage, stabilizers, binders, fluidization auxiliaries, hardening preventives, flocculants, antioxidants, floating agents, antifoaming agents, antifreeze agents, antiseptics, moisture removers, ultraviolet absorbers, ultraviolet scattering agents, coloring agents and suspension-stabilizers, to prepare microbicidal compositions of the present invention by the per se known methods. Namely, by mixing comound (I0) or salts thereof, liquid carriers or solid carriers, if necessary, various additives mentioned above, and other active ingredients of pesticides uniformly.
Emulsions of the present invention, for example, can be prepared by mixing and dissolving uniformly compound (I0) or salts thereof, emulsifiers, organic solvents, and so on. Granules and wettable granules of the present invention, for example, can be manufactured by mixing uniformly compound (I0) or salts thereof, dispersing agents (surfactants), binders, fillers (or solid carriers) and so on, uniformly, and then granulating.
Powders (DL powders and so on) of the present invention, for example, can be manufactured by mixing compound (I0) or salts thereof with fillers (or solid carriers) uniformly and pulverizing the resulting mixture. Flowable preparations of the present invention can be manufactured by mixing, dispersing compound (I0) or salts thereof, dispersing agents and so on with a mixer, and then by wet-pulverizing the resulting mixture by means of dynomill, and so on. Jumbo preparations, for example, can be manufactured by mixing compound (I0) or salts thereof with dispersing agents (surfactants), binders, floating agents, fillers (or solid carriers) uniformly, and by granulating the resulting mixture. Jambo formulations, powders, granules, wettable granules, hydrates and so on can be packed into water-soluble film-packages of 20 to 200 g each, for the sake of convenience in spraying. As the water-soluble films, there may be mentioned those of polyvinyl alcohol, carboxymethyl cellulose, starch, gelatin, polyvinylpyrrolidone, polyacrylic acid or salts thereof, pullulan (trade name: polysaccharide of a kind of starch), PAOGEN (Trade Name: a thermoelastic water soluble polymer), and so on.
As liquid carriers (solvents) appropriate for use, there may be mentioned, for example, water, alcohols such as methanol, ethanol, propanol, isopropanol, ethylene glycol, and so on, ketones such as acetone and methyl ethyl ketone, and so on, ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, and soon, aliphatic hydrocarobons such as kerosene, paraffin, fuel oil, machine oil, and edible oil, and so on, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, methylnaphthalene, and so on, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and so on, acid amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and so on, esters such as ethyl acetate, butyl acetate, fatty acid glycerol esters, and so on, and nitrites such as acetonitrile, propionitrile,and so on. These solvents can be used by mixing one or more than two (preferably not less than one nor more than three) of them in appropriate ratios. As solid carriers (diluents, fillers), there may be mentioned, for example, vegetable powders such as soybean powder, tobacco powder, wheat flour, wood flour, and so on, mineral powder, for example, clays such as kaolin, bentonite, acid clay, and so on, talcs such as talcum powder, agalmatolite powder, and so on, silicate minerals such as diatomaceous earth, mica, and so on, calcium carbonate, alumina, sulfur powder, activated carbon, and so on. These fillers can be used by mixing one or more than two (preferably not less than one nor more than three) of them in appropriate ratios. Further, as the ointment bases, there may be used, for example, one or more than two (preferably not less than one nor more than three) of polyethylene glycol, pectin, polyol higher fatty acid esters such as glycerol mono-stearic acid ester, and so on, cellulose derivatives such as methyl cellulose, and so on, sodium alginate, bentonite, higher alcohols, polyols such as glycerol, and so on, vaseline, white Vaseline, liquid paraffin, lard, various vegetable oils, lanoline, dehydrated lanoline, hydrogenated oil, resins, or mixtures of these substances with various surfactants described below appropriately.
As surfactants which may be used as emulsifiers, spreading agents, penetrants, moistening agents, dispersing agents, there may be mentioned nonionic surfactants such as soaps, polyoxyethylene alkylethers (NEWKALGEN FS4(trademark) (TM means trademark.), NOIGEN EA-177(trademark), NOIGEN ET83(trademark), NOIGEN ET157(trademark) and so on), polyoxyethylene alkylphenyl ethers, polyoxyethylene nonylphenyl ethers (NONIPOL20(trademark), NONIPOL100(trademark) and so on), polyoxyethylene alkylaryl ethers [for example, NOIGEN EA142(trademark), NOIGEN EA92(trademark); manufacured by Dai-ichi Kogyo Seiyaku Co., Ltd., NONAL(trademark); manufactured by Toho Chemical Industry Co., Ltd.], polyethyleneglycol ethers [for example, NONIPOL85(trademark), NONIPOL160(trademark); manufactured by Sanyo Chemical Industries Ltd.], polyol esters [for example, Tween 20(trademark), Tween80(trademark); manufactured by KAO Corp.], polyoxyethylene polyoxypropylene ethers, polyoxyethylene distylenated phenylether (NOIGEN EA87(trademark), NOIGEN EA177(trademark) and so on), polyoxyethylene alkylesters (ionetMO20(trademark), ionetMO600(trademark), and so on), sorbitan fatty acid esters (LEODOL SP-S10(trademark), LEODOL TW-S20(trademark) and so on), polyoxyethylene sorbitan fatty acid esters, block copolymer of ethylene oxide with propylene oxide (NEWPOL PE64(trademark)), higher fatty acid alkanol amides, alkylmaleic acid copolymer (DEMOL EP(trademark) and so on); cationic surfactants such as alkylamine salts and tert-ammonium salts, and so on; anionic surfactants such as alkylsulfuric acid salts [for example, EMAL10(trademark), EMAL40(trademark); manufactured by KAO Corp.], alkylsulfonic acid salts such as [for example, NEOGEN(trademark), NEOGEN T(trademark) manufactured by Dai-ichi Kogyo Seiyaku Co.,Ltd., NEOPEREX; manufactured by KAO Corp.], polymeric compounds such as naphtahlenesulfonic acid polycondensation product metal salts, formalin condensate of naphthalenesulfonic acid salts(NEWKALGEN FS4(trademark) and so on), alkylnaphthalene sulfonic acid salts (SOLPOL5115(trademark) and so on), ligninsulfonic acid metal salts, alkyl aryl sulfonic acid salts, alkyl arylsulfonate sulfate, and so on, anionic surfactant such as polynaphthylmethanesulfonic acid salts, polystyrenesulfonic acid sodium salt, polycarboxylic acid metal salts, polyoxyethylen histhylyl phenylether sulfate ammonium, higher alcohol sulfonic acid salts, higher alcohol ether sulfonic acid salts, dialkylsulfosuccinate (NEWKALGEN EP70P(trademark) and so on), and higher fatty acid alkali metal salts, and so on.
As salts, sodium salts, potassium salts, ammonium salts, diethanolamine salts, triethanolamine salts, monoisopropanolamine salts, diisopropanolamine salts, triisopropanolamine salts, other tertiary amine salts such as dialkyldimethylammonium salts, and so on can be used (applied, employed), in an extent where the function of the surfactants is not influenced.
As spreading agents, anionic surfactants, among surfactants mentioned above, which contain tert-amines as cationic part [for example, dialkyl dimethyl ammonium salts of polynaphthylmethanesulfonic acid such as Needs(trademark) (marketed by KUMIAI Chemical, The material is manufactured by KAO Corp.)] can be used preferable.
As stabilizers, compounds having epoxy groups, antioxidants [for example, dibutylhydroxytoluene (BHT), butylhydroxy anisole (BHA), tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymeth yl]methane (Irganox 1010), DL-tocopherol, propyl gallate, erythorbic acid, sodium erythorbate, isopropyl citrate, and so on], phosphoric acid, PAP auxiliary agents (isopropyl acid phosphate), cyclodextrin (TOYODELLINE P), tall oil (Hartall fatty acids), and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As binders, dextrin, pregelatinized starch, polyvinyl alcohol, Arabic gum, sodium alginate, polyvinylpyrrolidone, glucose, saccharose, mannitol, sorbitol, and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As fluidization auxiliaries, PAP auxiliaries (for example,isopropyl acidphosphate) and talc, and so on can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriateratios when used.
As hardening preventives, white carbon, diatomaceous earth, magnecium stearate, aluminum oxide, titanium dioxide, and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As flocculants, liquid paraffin, ethylene glycol, diethylene glycol, triethylene glycol, isobutylene polymers (for example, IP Solvent), and so on,be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As antioxidants, dibutylhydroxytoluene, 4,4-thiobis-6-tert-butyl-3-methylphenol, butylhydroxyanisole, paraoctylphenol, mono- (or di- or tri-)(xcex1-methylbenzyl)phenol, 2,6-di-tert-butyl-4-methylphenol, tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane, and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As floating agents, used especially for manufactureing jambo formulation, powder bases which have the specific gravity of 1 or less than 1 (preferably 1 to 0.5) and the particle diameter of 600 xcexcm or less, more preferably from 600 m to 10 xcexcm, are preferably used. As inorganic floating agents, there can be mentioned those which can be obtained by calcinating natural glass-like materials and consist of glass particles with one or several air bubbles, in them, for example perlite made from pearlite and orobsidian, Shirasu-balloon (Trade Name) made from Shirasu, vermiculite made from Hiru-ishi and phyllite (Trade Name)which is one of aluminosilicates and can be obtained by calcination, and so on, and as organic floating agents, there can be mentioned such substances called in general wax-like materials, for example, higher fatty acids such as stearic acid and palmitic acid which are solid at room temperatures, higher alcohols such as stearyl alcohols, and paraffin wax, and so on. However, as these wax-like materials are water-repellant, they have tendency to prevent water from penetrating into them and to prevent the agrochemical active constituents which are confined in them from leaking and spreading into surrounding water, thus making it reasonable to make use of such wax-like organic floating agents in a mixture with the glass hollow bodies mentioned above.
As antifoaming agents, silicone antifoaming agents (for example, Antifoam E20), and so on, can be preferably used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As antifreezing agents, ethylene glycol, diethylene glycol, polyethylene glycol, glycerol, and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As antiseptic agents, butylparaben and potassium sorbate, and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As moisture removers, anhydrous gypsum and silica gel powder, and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As ultraviolet absorbers, 2-(2xe2x80x2-hydroxy-5xe2x80x2-methylphenyl)benzotriazole, 2-ethoxy-2xe2x80x2-methyloxalic acid bisanilide, dimethyl succinate-1-(2-hydroxyethyl)-4-hydroxy-2xe2x80x2,2,6,6-tetramethylpiperidine polycondensates and so on, can be used preferably. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As ultraviolet scattering agents, titanium dioxide, and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As coloring agents, CYANINEGREEN G, ERIOGREEN B400, and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used.
As suspension stabilizers, polyvinyl alcohol (GOHSENOL GH17 and so on), clay minerals (Kunipia F, VEEGUM R, and so on), silicone dioxide (AEROSIL COK84, and so on), and so on, can be used. One or more than two (preferably not less than one nor more than three) of these compounds can be admixed in appropriate ratios when used. Jumbo preparations, powders, granules wettable granules, hydrates and so on can be packed into water-soluble film-packages of 20 to 200 g each, for convenience in spraying. As the said water-soluble film, there may be mentioned polyvinyl alcohol, carboxymethyl cellulose, starch, gelatin, polyvinylpyrrolidone, polyacrylic acid or salts thereof, Pullulan (Trade Name: polysaccharide of a kind of starch), PAOGEN (trade name: a thermoelastic water soluble polymer), and so on.
Furthermore, compound (I0) or salts thereof can be combined and used with, for example, insecticides, acaricide,nematocides, herbicides, plant hormones, plant growth regulators, antimicrobials, synergists, attractants, repellants, pigments, fertilizers, and so on.
Thus, the present invention includes also microbiocides for agricultural or horticultural use which contain both the compound (I0) or salts thereof and other active agrochmical constituents.
The said other agrochemical constituents may be contained in the same preparation with compound (I0) or salts thereof or may be formulated into separate preparations which can be mixed just before use.
Representative insecticides, acaricide and nematocides which can be used by admixing with compound (I0) or salts thereof are as follows: acephate, acetamiprid, acrinathrin, alanycarb, aldrin, allethrin, Aluminium phosphide, amitraz, Arsenic acid, avermectin-B, bendiocarb,benfuracarb, bensultap, benzoximate, bifenthrin, bromopropylate, buprofezin, Calcium cyanamide, Calcium polysulfide, carbaryl:NAC, carbofuran, carbosulfan, cartap, chlordane, chlorfenvinphos:CVP, chlorfluazuron, chlorphenapyr, chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyanophos:CYAP, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, cyromazine, dichlorodiisopropyl ether, Dxe2x80x94D(1,3-Dichloropropene), DDT, deltamethrin, diafenthiuron, diazinon, dichlofenthion, dichlorvos:DDVP, dicofol, dieldrin, dienochlor, diflubenzuron, dimethoate, dimethylvinphos, disulfoton, DSP, endosulfan, EPN, esfenvalerate, ethion, ethofenprox, ethoprophos, etoxazole, fenbutatin oxide, fenitrothion:MEP, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenvalerate, fipronil, fluazinam, flucythrinate, flufenoxuron, flupyrazofos, fluvalinate, formetanate, formothion, fosthiazate, furathiocarb, halfenprox, hexaflumuron, hexythiazox, Hydrogen phosphide, imidacloprid, isofenphos, isoprocarb, isoxathion, malathion, mesulfenfos, metam-ammonium, metam-sodium, methidathion, methiocarb, methomyl, methoxychlor, methoxyfenozide, Methyl bromide, metolcarb:MTMC, milbemycin-A, monocrotophos, naled:BRP, nicotine-sulfate, nidinotefuran, nitenpyram, oxamyl, oxydeprofos:ESP, parathion, permethrin, phenthoate:PAP, phosalone, phosmet:PMP, pirimicarb, pirimiphos-methyl, Potassium oleate, profenofos, propaphos, propargite:BPPS, propoxur, prothiofos, protrifenbute, pymetrozine, pyraclofos, pyrethrins, pyridaben, pyridafenthion, pyrimidifen, pyriproxyfen, quinalphos, resmethrin, salithion, silafluofen, Sulfur, sulprofos, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, temephos, tetrachlorvinphos, tetradifon, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiometon, tolfenpyrad, tralomethrin, trichlorfon:DEP, triflumuron, vamidothion, XMC.
Representative antimicrobials which can be used by admixing with compound (I0) or salts thereof are as follows: for example, acetic acid, acibenzolar-S-methyl, amobam, anilazine, azoxystrobin, benomyl, benthiazole, bitertanol, blasticidin-S, Bordeaux mixture, bromuconazole, buthiobate, Calcium hypochlorite, Calcium polysulfide, captan, carbendazol, carpropamid, IKF-916 (4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide), chloroneb, chloropicrin, chlorothalonil:TPN, Cinnamaldehyde, RH-7281 (3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)4-methylbenzamide), CNA (2,6-Dichloro-4-nitroaniline), Copper hydroxide, Copper sulfate, AC382042 (N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) propionamide(R,S)-and(R,R)-and(S,R)-and(S,S)), cymoxanil, cyproconazole, cyprodinil, dazomet, dichlofluanid, Dxe2x80x94D (1,3-Dichloropropene), diclocymet, diclomezine, diethofencarb, difenoconazole,diflumetorim, dimethirimol, dimethomorph, diniconazole-M, dinocap, Nickel dimethyldithiocarbamate, etridiazole, famoxadone, fenarimol, fenbuconazole, Fendazosulam, fenhexamid, NNF-9425:fenoxanil, fenpiclonil, fentiazon, fentin hydroxide, ferimzone, fluazinam, fludioxonil,RPA-403397:flumetover, fluoroimide, fluquinconazole, flusulfamide, flutolanil, fosetyl-Al, fthalide, furametpyr, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadinetriacetate, iodocarb, ipconazole, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metalaxyl-M, metam-sodium, methasulfocarb, Methyl bromide, RPA407213 (s-5-methyl-2-methylthio-5-phenyl-3-phenylamino-3,5-dihydroimidazol-4-one), metominostrobin, mildiomycin, milneb, myclobutanil, nabam, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin, oxytetracycline, pefurazoate, penconazole, pencycuron, picoxystrobin, polycarbamate, polyoxin, Potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb-hydrochloride, propiconaole, propineb, pyrazophos, pyributicarb, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene:PCNB, MON65500:silthiopham, sipconazole, Sodium bicarbonate, sodium hypochlorite, SSF-129 ((E)-2[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyimino-N-methylacetamide), streptomycin, Sulfur, tebuconazole, tecloftalam, tetraconazole, thiabendazole, thiram:TMTD, thifluzamide, thiophanate-methyl, triadimefon, triadimenol, tricyclazole, tridemorph, triflumizole, trifloxystrobin, triforine, validamycin, vinclozolin, zineb, ziram.
Representative herbicides, plant hormones, and plant growth regulators which can be used by admixing with compound (I0) or salts thereof are as follows: Abscisic acid, acetochlor, acifluorfen-sodium, alachlor, alloxydim, ametryn, amidosulfuron, amiprofos-methyl, ancymidol, asulam, atrazine, azimsulfuron, benfluralin, benfuresate, bensulfuron-methyl, bensulide:SAP, bentazone, benthiocarb, benzamizole, benzfendizone, benzofenap, Benzyl adenine, bialaphos, bifenox, Brassinolide, bromacil, bromobutide, butachlor, butafenacil, butamifos, butylate, cafenstrole, Calcium carbonate, Calcium peroxide, carbaryl, chlomethoxynil, chloridazon, chlorimuron-ethyl, chlorphthlim, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid:DCBN, choline chloride, cinmethylin, cinosulfuron, clethodim, clomeprop, cloxyfonac-sodium, 4-CPA (4-chlorophenoxyacetic acid), cumyluron,cyanazine, cyclosulfamron, cyhalofop-butyl, 2,4-D salts (2,4-Dichlorophenoxyacetic acid salts), dichlorprop:2,4-DP, daimuron, dalapon:DPA, daminozide, dazomet, n-Decyl alcohol, dicamba sodium:MDBA, dichlobenil:DBN, diflufenican, dimepiperate, dimethametryn, dimethenamid, diquat, dithiopyr, diuron, endothal, esprocarb, ethephon, ethidimuron, ethoxysulfuron, ethychlozate, etobenzanid, fenarimol, fenoxaprop-ethyl, fentrazamide, flazasulfuron, florasulam, fluazifop-butyl, flumioxazin, flupropanate-sodium, flurprimidol, fluthiacet-methyl, forchlorfenuron, formesafen, gibberellin, glufosinate, glyphosate, halosulfuron-methyl, hexazinone, imazamox, imazapyr, imazaquin, imazosulfuron, inabenfide, Indole acetic acid:IAA, Indole butyric acid, ioxynil-octanoate, isouron, karbutilate, lactofen, lenacil, linuron, Maleic hydrazide, mecoprop:MCPP, MCP salts (2-Methyl-4-chlorophenoxyacetic acid salts), MCPA.thioethyl (MCPA-thioethyl), MCPB (2-Methyl-4-chlorophenoxybutanoic acid ethyl ester), mefenacet, mefluidide, mepiquat, methyl daimuron, metolachlor, metribuzin, metsulfuron-methyl, molinate, AND (1-naphthaleneacetamide), naproanilide, napropamide, nicosulfuron, orbencarb, oxadiazon, oxaziclomefone, oxine-sulfate, paclobutrazol, paraquat, Pelargonic acid, pendimethalin, pentoxazone, pethoxamide, phenmedipham, picloram, piperonyl butoxide, piperophos, pretilachlor, primisulfuronmethyl, procarbazone, prodiamine, prohexadione-calcium, prometryn, propanil, propyzamide, pyraflufen-ethyl, pyrazolate, pyrazosulfuron-ethyl, pyrazoxyfen, pyributicarb, pyridate, pyriminobac-methyl, pyrithiobac, quiclorac, quinoclamine, quizalofop-ethy, rimsulfuron, sethoxydim, siduron, simazine, simetryn, Sodium chlorate, sulfosulfuron, swep:MCC, tebuthiuron, terbacil, terbucarb:MBPMC, thenylchlor, thiazafluron, thifensulfuron-methyl, triaziflam, triclopyr, tridiphane, trifluralin, trinexapac-ethyl, tritosulfuron, uniconazole-P, vemolate:PPTC.
Among xe2x80x9cother active agrochemical constituentsxe2x80x9d mentioned above, antimicrobial active constituents and insecticidal active constituents are especially preferable.
Furthermore, as the said antimicrobial active constituents, in addition to azoxystrobin, chlorothalonil, hexaconazole, iminoctadine, mepanipyrim, kresoxim-methyl and iprodione, there may be mentioned carpropamid, diclocymet, probenazole, tricyclazole, pyroquilon, isoprothiolane, acibenzolar-S-methyl, as agents for treating the soil, seed of rice and for spraying on the water surface of the rice cultivation. And as agents for spraying on the leaves and stems of the rice plant, carpropamid, diclocymet, probenazole, tricyclazole, pyroquilon, isoprothiolane, acibenzolar-S-methyl, validamycin A, ferimzone, fthalide and so on, can be used more preferably, and among said agents, validamycin A, ferimzone and fthalide can be used most preferably.
Futhermore, as the said inscticidal active constituents, clothianidin [1-(2-chlorothiazol-5-ylmethyl)-3-methyl-2-nitroguanidine], nitenpyram [(E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-Nxe2x80x2-methyl-2-nitrovin ylydeneamine], cartap hydrochloride [1,3-bis(carbamoylthio)-2-(N,N-di-methylamino)propane hydrochloride], bensultap [S,Sxe2x80x2-2-dimethyl-amminotrimethylenexe2x95x90di(benzenethiosulfonate)], pyraclofos [(RS)-[O-1-(4-chlorophenyl)pyrazol-4-yl]xe2x95x90O-ethylxe2x95x90S-propylxe2x95x90phosphorothioate], and so on, can be used especially preferably.
Thus, the present invention includes
[1] A microbicide for agricultural or horticultural use which contains compound (I) or salts thereof and other agrochemically active constituents,
[2] A microbicide for agricultural or horticultural use which contains compound (II) or salts thereof and other agrochemically active constituents,
[3] A microbicide for agricultural or horticultural use which contains compound (III) or salts thereof and other agrochemical active constituents,
[4] A microbicide for agricultural or horticultural use which contains compound (IV) or salts thereof and other agrochemical active constituents,
[5] A microbicide for agricultural or horticultural use which contains compound (V) or salts thereof and other agrochemical active constituents,
[6] A microbicide for agricultural or horticultural use which contains compound (VI) or salts thereof and other agrochemical active constituents,
[7] A microbicide for agricultural or horticultural use which contains compound (IIxe2x80x2) which will be described below or salts thereof and other agrochemically active constituents,
[8] A microbicide for agricultural or horticultural use described in [1] to [7] above, wherein the other agrochemical active constituents are insecticides,
[9] A microbicide for agricultural or horticultural use described in [8], wherein the other agrochemical active constituents are more than one of those selected from bensultap, cartap, clothianidin, nitenpyram and pyraclofos,
[10] A microbicide described in [1] to [7] above, wherein the other agrochemical active constituents are antimicrobial active constituents,
[11] A microbicide for agricultural or horticultural use described in [10] above, wherein the other agrochemical active constituents are more than one of those selected from azoxystrobin, chlorothalonil, hexaconazole, iminoctadine, mepanipyrim, kresoxim-methyl, iprodione, ferimzone, fthalide and validamycin, and
[12] A method to increment the microbicidal action of compound (I), (II), (III), (IV), (V), (VI) or (IIxe2x80x2) described below, or salts thereof which comprises using them in combination with other agrochemically active constituents.
Among the said compound (I), (II), (III), (IV), (V), (VI) which may be used in combination with other agrochemical active constituents or (IIxe2x80x2) which will be described below, or salts thereof, compound (I), (II), (III), (VI) or (IIxe2x80x2) or salts thereof are more preferable, and compound (II), (VI) or (IIxe2x80x2) or salts thereof are especially preferable.
Specific examples of the more preferable compound are 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 2xe2x80x2,4xe2x80x2-dinitro-N-ethyl-p-toluenesulfonanilide, 2xe2x80x2,4xe2x80x2-dicyano-N-ethyl-p-toluensulfonanilide, 4xe2x80x2-chloro-N-isopropyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 4xe2x80x2-fluoro-N-isopropyl-2xe2x80x2-nitro-p-toluene-sulfonanilide, 4xe2x80x2-cyano-N-isopropyl-2xe2x80x2-nitro-p-toluenesulfonanilide, 4xe2x80x2-chloro-N-isopropyl-2xe2x80x2-cyano-p-toluenesulfonanilide, 2xe2x80x2,4xe2x80x2-dinitro-N-iso-propyl-p-toluenesulfoanilide, 4xe2x80x2-nitro-N-isopropyl-2xe2x80x2-cyano-p-toluenesulfonanilide, 2xe2x80x2-cyano-N-methoxy-4xe2x80x2-nitro-p-toluenesulfonanilide, or 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesufonanilide or salts thereof.
In those compositions which contain compound (I0) [for example, compound (I), (II), (III), (IV), (V), (VI) or (IIxe2x80x2) which will be described below] or salts thereof and nitenpyram, it may be advantageous to make first an inclusion compound of nitenpyram with cyclodextrin, for example, TOYODERIN (commercial product name), and then the resulting inclusion compound come into the composition in order to enhance stability of the composition.
These compositions may further contain not less than one kind (more preferably not less than one nor more than three kinds) of other agrochemical active constituents,(for example, insecticidal, acaricidal, antimicrobial active components, and so on). As such compositions, there can be mentioned compositions which contain compound (I0) [for example, compound (I), (II), (III), (IV), (V), (VI) or (IIxe2x80x2) which will be described below] or salts thereof, ferimzone and fthalide, and compositions which contain compound (I0) [compound (I), (II), (III), (IV), (V), (VI) or (IIxe2x80x2) which will be described below] or salts thereof, validamycin, ferimzone and fthalide and so on.
More preferable embodiments of composition which contain other agrochemically active constituents are as follows:
(i) A microbicide for agricultural or horticultural use which contains 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide or salts thereof and ferimzone.
(ii) A microbicide for agricultural or horticultural use which contains 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide or salts thereof and fthalide.
(iii) A microbicide for agricultural or horticultural use which contains 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide or salts thereof and validamycin.
(iv) An insecticide/microbicide for agricultural or horticultural use which contains 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide or salts thereof and bensultap.
(v) An insecticide/microbicide for agricultural or horticultural use which contains 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide or salts thereof and cartap,
(vi) An insecticide/microbicide for agricultural or horticultural use which contains 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide or salts thereof and clothianidin.
(vii) An insecticide/microbicide for agricultural or horticultural use which contains 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide or salts thereof and nitenpyram.
(viii) An insecticide/microbicide for agricultural or horticultural use which contains 4xe2x80x2-chloro-N-ethyl-2xe2x80x2-nitro-p-toluenesulfonanilide or salts thereof and pyraclofos.
(ix) A microbicide for agricultural or horticultural use which contains 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesulfonanilide or salts thereof and ferimzone.
(x) A microbicide for agricultural or horticultural use which contains 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesulfonanilide or salts thereof and fthalide.
(xi) A microbicide for agricultural or horticultural use which contains 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesulfonanilide or salts thereof and validamycin.
(xii) An insecticide/microbicide for agricultural or horticultural use which contains 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesulfonanilide or salts thereof and bensultap.
(xiii) An insecticide/microbicide for agricultural or horticultural use which contains 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesulfonanilide or salts thereof and cartap.
(xiv) An insecticide/microbicide for agricultural or horticultural use which contains 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesulfonanilide or salts thereof and chlothianidin.
(xv) An insecticide/microbicide for agricultural or horticultural use which contains 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesulfonanilide or salts thereof and nitenpyram.
(xvi) An insecticide/microbicide for agricultural or horticultural use which contains 2xe2x80x2,4xe2x80x2-dinitro-N-methoxy-p-toluenesulfonanilide or salts thereof and pyraclofos.
Regarding [12] mentioned above, the present inventors have found that using the compound (I), (II), (III), (IV), (V), (VI) or (IIxe2x80x2) which will be described below, or salts thereof of the present invention in combination with other agrochemical active constituents may give an increased effectiveness in their microbicidal action over that which may be obtained when each of those agents is used singly.
Those microbiocides obtained by combining the sulfonamide derivatives of the present invention described above [for example, compound (I), (II), (III), (IV), (V), (VI) or compound (IIxe2x80x2) which will be described below] and other agrochemical active constituents can exert excellent effectiveness in that (1) the antimicrobial/insecticidal/acaricidal/nematocidal effectiveness may be increased relative to the cases where each agent is used separately, (2) an immediate antimicrobial/insecticidal/acaricidal/nematocidal effect is gained, (3) a wide antimicrobial/insecticidal/acaricidal/nematocidal spectrum and a sustained effectiveness are gained, which has not been realized with known antimicrobicide/insecticide/acaricide/nematocide, (4) the amounts of agents needed can be decreased compared to the cases where each agents is used singly, and (5) a more reliable protective effect can be expected compared to the cases where each agent is used singly against each harmful organism.
As the diseases protected using compound (I0) or salts are, there may be mentioned, for example, diseases of rice plant such as rice blast (Pyricularia oryzae), Helminthosporium leaf blight (Helminthosporium oryzae, Cochliobolus miyabeanus), Bakanae disease (Gibberella fujikuroi), seedling blight (Rhizopus oryzae), sheath blight (Rhizoctonia solani), and so on, those of oat such as crown rust (Puccinia coronata), and so on, those of barley such as powdery mildew (Erysiphe graminis), scald (Rhynchsporium secalis), spot-blotch (Cochliobolus sativus), yellow mottleleaf (Helminthosporium gramineum, Pyrenophora gramineum), net blotch (Pyrenophra teres), stinking smut (Tilletia caries), loose smut (Ustilago nuda), and so on, those of wheat such as powdery mildew (Erysiphe graminis), glume-blotch (Leptosphaeria nodorum, Septoria nodorum), stripe rust (Puccinia striiformis), Typhula snow blight (Typhula incarnate), eye spot (Pseudocercosporella herpotrichoides), snow mold (Calonectria graminicola, Fusarium nivale), stem rust (Puccinia graminis), black snow blight (Typhula ishikariensis), scab (Gibberella zeae), leaf rust (Puccinia recondita, Puccinia triticina), stripe (Helminthosporium gramineum), stinking smut (Tilletia caries), speckled leaf blight (Septoria tritici), loose smut (Ustilago tritici), and so on, those of corn such as damping-off (Pythium debaryanum), and so on, those of rye such as purple snow mold (Fusarium nivale), and so on, those of potato such as foot rot (Phytophthora infestans), and so on, those of tabacco plant such as downy mildew (Peronospora tabacina), foot rot (Phytophthora parasitica var), septoria blight (Cercospora nicotianae), mosaic disease (tobacco mosaic virus), and so on, those of sugar beet such as leaf spot (Cercospora beticola), damping-off (Pythium debaryanum, Rhizoctonia solani), take-all (Pythium aphanidermatum), and so on, those of paprika such as gray mold (Botrytis cinerea), and so on, those of kidney bean such as gray mold (Botrytis cinerea), sclerotinia seed rot (sclerotial rot) (Sclerotinia sclerotiorum), southern blight (Corticium rolfsii), and so on, those of broad bean such as powdery mildew (Erysiphe polygoni, Sphaerotheca fuliginea), rust (Uromyces fabae, Uromyces phaseoli), gray mold (Botrytis cinerea), and so on, those of peanut such as Ascochyta spot (Mycosphaerella arachidicola), and so on, those of cabbage such as damping blight (Rhizoctonia solani), and so on, those of cucumber such as powdery mildew (Sphaerotheca fuliginea), stem rot (Fusarium oxysporum), gummy stem blight (Mycosphaerella melonis), downy mildew (Pseudoperonospora cubensis), gray mold (Botrytis cinerea), sclerotial seed rot (Sclerotinia sclerotiorum), anthracnose (Colletotrichum lagenarium), damping blight (Fusarium oxysporum, Pythium aphanidermatum, Rhizoctonia solani), mosaic disease (Cucumber mosaic virus), and so on, those of KOMATSUNA such as Alternaria sooty spot (Alternaria brassicicola), club root (Plasmodiophora brassicae), and so on, those of celery such as speckled leaf blotch (Septoria apii), and soon, those of radish such as yellows (Fusarium oxysporum), and so on, those of tomato such as Fusarium wilt (Fusarium oxysporum), foot rot (Phytophthora infestans), ring leaf-spot (Alternaria solani), gray mold (Botrytis cinerea), leaf blight (Phytophthora capsici), black rot (Alternaria tomato), and so on, those of eggplant such as brown rot (Phytophthora capsici), Verticillium wilt (Verticillium albo-atrum), and so on, those of Chinese cabbage such as black rot (Alternaria japonica), club root (Plasmodiophora brassicae), and so on, those of sweet pepper such as foot rot (Phytophthora capsici), gray mold (Botrytis cinerea), and so on, those of lettuce such as gray mold (Botrytis cinerea), and so on, those of citrus fruits such as pod and stem blight (Diaporthe citri), and so on, those of pear such as scab (Venturia nashicola), black rot (Alternaria kikuchiana), brown-spot (Gymnosporangium haraeanum), and so on, those of grape such as downy mildew (Plasmopara viticola), gray mold (Botrytis cinerea), Sphaceloma scab (Elsinoe ampelina), and so on, those of peach such as leaf curl (Taphrina deformans), shot hole (Mycosphaerella cerasella), and so on, those of apple such as powdery mildew (Podosphaera leucotria), scab (Cladsporium carpophilum), gray mold (Botrytis cinerea), black rot (Venturia inaequalis), brown spot (Gymnosporangium yamadae), white root rot (Rosellinia nectrix), Alternaria leaf spot (Alternaria mali), and so on, and other deseases of grains, fruits and vegetables such as oil-seed rape, sunflower, carrot, pepper, strawberry, melon, kiwi fruit, onion, leek, sweet potato, fig, ume, asparagus, persimmon, soybean, adzukibean, watermelon, crown daisy, spinach, tea and so on. Thus, compound (I0) or salts thereof show high activities against deseases caused by microorganisms of, especially, the genus Pyricularia, Cochliobolus, Curvularia, Pyrenophora, Alternaria, and others akin to them. As for examples of deseases caused by those microbes, there may be mentioned rice blast, Helminthosporium leaf spot, and discolored rice grains of rice plant, spot-blotch, stripe, and net blotch of barley, stripe and spot-blotch of wheat, Helminthosporium leaf spot of corn, early blight of potato, Alternaria sooty spot of HAKUSAI, ring leaf-spot and black rot of tomato, black rot of Chinese cabbage, black rot of pear, and Alternaria leaf spot of apple, and so on.
Among compound (I0) or salts thereof mentioned above, those which have, as Z0, a group represented by xe2x80x94OR3 or salts thereof show excellent protective effectiveness against clubroot disease in the plants of Brassica family (for example, canola, turnip, cauliflower, cabbage, KOMATSUNA, rape seed, and Chinese cabbage.
Among them, compound (I), (II) and (III) mentioned-above or salts thereof, which have , as Z1, Z2 and Z3, a group represented by xe2x80x94OR3, respectively, are more preferable, especially preferable being compound (IIxe2x80x2) below or salts thereof.
Compound (IIxe2x80x2) are compounds represented by the Formula (IIxe2x80x2): 
or salts thereof,
[where A2xe2x80x2, X2xe2x80x2 and B2xe2x80x2 have the same meanings as A2, X2 and B2 mentioned above, respectively, Z2xe2x80x2 is a group represented by xe2x80x94OR3 (R3 has the same meaning as that mentioned above)].
Among the compounds included in compound (IIxe2x80x2), preferable compounds or salts thereof are those which have, as A2xe2x80x2, either (1) a C6-14 aryl group which may substituted with 1 to 5 substituents selected from (i) a C1-4 alkyl group which may be substituted with 1 to 5 halogens, (ii) a C1-4 alkoxy group which may be substituted with 1 to 5 halogens,(iii) an amino group which may be substituted with 1 or 2 C1-4 alkyl-carbonyl, (iv) the C1-4 alkoxy-carbonyl group, (v) halogen atoms, (vi) the cyano group, and (vii) the nitro group, or (2) the thenyl group, the triazolyl group, the imidazolyl group, the isooxazolyl group, the pyrazolyl group, the pyridyl group, the quinolyl group, the benzothiadiazolyl group, the imidazothiazolyl group or the imidazopyridyl group, each of which may be substituted with 1 to 5 substituents selected from (i) the C1-4 alkyl group, (ii) the C1-4 alkoxy-carbonyl group, (iii) the carbamoyl group, (iv) mono- or di-C1-4 alkylcarbamoyl group, (v) the C1-4 alkylsulfonyl group, (vi) halogen atoms, (vii) the carboxyl group and (viii) the cyano group, as X2 is (1) the chemical bond, (2) the methylene group which may be substituted with 1 or 2 C1-4 alkyl, or (3) the vinylene group which may be substituted with 1 or 2 C1-4 alkyl, B2 is a C6-14 aryl group which may be substituted with 1 to 5 Substituents selected from (1) a C1-4 alkyl group which may be substituted with 1 to 5 substituents such as halogen, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkyl-hydrazono and C1-4 alkylthio, (2) the C2-4 alkynyl group, (3) the hydroxy group, (4) the C1-4 alkoxy group which may be substituted with 1 to 5 substituents selected from halogens and C1-4 alkoxy, (5) the C1-4 alkyl-carbonyloxy group, (6) the C1-4 alkylthio group, (7) the C1-4 alkylsulfinyl group, (8) the C1-4 alkylsulfonyl group, (9) mono- or di-C1-4 alkylsulfamoyl group, (10) the amino group, (11) the formyl group, (12) the C1-4 alkoxy-carbonyl group, (13) the carbamoyl group, (14) mono- or di-C1-4 alkylcarbamoyl group, (15) the thiocarbamoyl group, (16) halogen atoms, (17) the carboxyl group, (18) the thiocyanato group, (19) the cyano group, (20) the nitroso group and (21) the nitro group, Z2 is a group which is represented by xe2x80x94OR3 (wherein R3 is a C1-4 alkyl group or a C1-4 alkyl-carbonyl group) or salts thereof.
More preferable embodiments of compound (IIxe2x80x2) or salts thereof are as follows:
Preferably, A2xe2x80x2 is (a) a phenyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl which may be substituted with 1 to 3 halogens, halogens and nitro, (b) a thienyl group which may be substituted with 1 to 3 halogens, or (c) a pyrazolyl group which may be substituted with 1 to 3 substituents selected from C1-4 alkyl and halogens, a phenyl group substituted with a methyl group at 4-position being especially preferable.
Preferably, B2xe2x80x2 is a phenyl group which may be substituted with substituents selected from (a) the C1-4 alkyl group which may be substituted with 1 to 5 (preferably with 1 to 3) halogen atoms, (b) halogen atoms (c) the cyano group and (d) the nitro group, especially preferable being phenyl groups which have substituents at the 2- or 4- position.
Z2 should preferably be a C1-4 alkoxy group or a C1-4 alkyl-carbonyloxy group, especially preferable being methoxy and ethoxy groups.
Preferably, X2 is a chemical bond (a single bond or a bond).
Those preferable features of A2xe2x80x2, B2xe2x80x2, Z2xe2x80x2 and X2xe2x80x2 mentioned in (1) to (4) above, may be combined together arbitrarily.
Since compound (I0) or salts thereof have microbicidal action and are of very low toxicity and safe to handle, they can be used as excellent microbicidal compositions. The compositions of the present invention can be used in a manner similar to the known microbicidal compositions, and can exert superior effect to the previously known compositions. The compositions of the present invention can be used by spraying them on the irrigated rice field, a field, an orchard, and non-cultivated land, and so on, by the per se known method. More specifically, they can be used, for example, by treating a seed bed with them, spraying them on the stem/leaves of the plants, spraying them in the water of the irrigated field, by treating seeds or the soil with them, and applying them directly on the stem of fluit trees. And, the amount used may be, in general, 0.3 g to 3000 g effective constituents per 1 hectare, or more preferably 50 g to 1000 g effective constituents(compound(I0) or salts thereof) per 1 hectare, although it can be altered within a wide range according to the time, place, and method of applying. Furthermore, in cases where the compositions of the present invention are wettable powders, they can be used by diluting them to adjust the final concentration of the effective constituents to a range of 0.1 to 1000 ppm, or more preferably to 10 to 500 ppm.
The contents of compound (I0) or salts thereof to the whole amount of the composition can usually be about 0.1 to 80 wt %, or more preferably about 1 to 20 wt % or so. More specifically, when they re used as an emulsion, liquids, wettable powders (for example wettable granules), aqueous suspensions, microemulsions and so on, they can be used in a ratio, in general, of about 1 to 80wt % or so, or more preferably of about 1 to 20 wt % or so, and when they are used as ointments or powders and so on, they can be used usually in a ratio of about 0.1 to 50 wt % or so, or more preferably in that of about 1 to 20 wt % or so. When they are used as granules, tablets, Jumbo agents and so on, they can be used usually in a ratio of about 5 to 50 wt % or so, or more preferably of about 1 to 20 wt % or so. The other agrochemical active constituents (for example, insecticides, acgaricides, herbicides and (or) microbicides) which may be mixed to prepare compositions of the present invention, can be used usually in a ratio of about 1 to 80 wt % or so, or more preferably in that of about 1 to 20 wt % or so to the whole amount of the compositions. The contents of the additives other than the active constituents mentioned above are in general about 0.001 to 99.9 wt % or so, or more preferably about 1 to 99 wt % or so, although they vary depending upon the kinds, contents or preparation form of the agrochemical active.
More specifically, it is preferable to add, to the total amount of the compositions, usually about 1-20 wt % or so, or more preferably about 1-15 wt % of surfactants, about 1-20 wt % or so fluidization auxiliaries, about 1-90 wt % or so, or more preferably about 1-70 wt % or so of carriers. To give more specific examples, in the cases where liquids are to be prepared, it is usually preferable to add about 1-20 wt % or so , or more preferably 1-10 wt % or so of surfactants, and 20-90 wt % or so of water. It is preferable to dilute emulsions or wettable powders (for example wettable granules) and so on to an appropriate volume (for example, to about 100 to 5000 times of volume), for example, with water and so on before use, and to spray it (them).
Compound (I0) or salts thereof can be manufactured, for example, according to the reaction equations (A), (B), (C) or by means of the synthetic method (D) given below:

Compound (I0) or salts thereof can be manufactured by making compounds XI which are obtainable by the reaction of sulfonylating agents represented by Formula (VII)
A0xe2x80x94X0xe2x80x94SO2xe2x80x94L
(wherein A0 and X0 have the same meanings as those mentioned above, and L is a leaving group) with amines represented by Formula (VIII)
H2Nxe2x80x94B0
(wherein B0 has the same meaning as mentioned above), or salts thereof or by the reaction of sulfonamides represented by Formula (IX)
A0xe2x80x94X0xe2x80x94SO2xe2x80x94NH2
(wherein the symbols have the same meanings as those mentioned above) or salts thereof, with the compounds represented by Formula (X)
Lxe2x80x2xe2x80x94B0
(wherein Lxe2x80x2 is a leaving group and B0 has the same meaning as mentioned above) or salts thereof to give the compounds represented y Formula (XI), (wherein each symbol has the same meaning as mentioned above) and Formula(XI): 
react with electrophiles of Formula (XII)
Z0xe2x80x94Lxe2x80x3
(wherein Lxe2x80x3 is a leaving group, and Z0 has the same meaning as mentioned above).
As the sulfonylating agent represented by Formula (VII), there can be mentioned, for example, sulfonyl chloride, sulfonyl bromide, and sulfonic anhydride, and so on.
As the leaving group represented by L, Lxe2x80x2 or Lxe2x80x3, there can be mentioned, for example, halogen atoms such as fluorine, chlorine, bromine, and iodine, a lower alkoxy (preferably a C1-4 alkoxy) group such as methoxy, ethoxy, propoxy, and so on, a phenoxy group, a lower alkylthio (preferably a C1-4 alkylthio) group such as methylthio, ethylthio, propylthio,and so on, a lower alkylsulfinyl (preferably a C1-4 alkylsulfinyl) group such as methylsulfinyl, ethylsulfinyl,propylsulfinyl, a lower alkylsulfonyl (preferably a C1-4 alkylsulfonyl) group such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, and so on, a lower alkylsulfonyloxy (preferably a C1-4 alkylsulfonyloxy) group such as methylsulfonyloxy, ethylsulfonyloxy, propylsulfonyloxy group, and so on, a trifluoromethylsulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, and so on.
{circle around (1)} The reaction of sulfonylating agents (VII) with amines (VIII) can be carried out according to the method described in, for example, The Journal of Pesticide Science Society of Japan 21,p31(1996), Japanese Patent Publication for Opposition 6836/1970, and so on. Japanese Publication Patent for Opposition 19199/1965, Japanese Patent for Laid-Open 31655/1982, Japanese Patent Application Laid-Open 219159/1983, Japanese Patent Application Laid-Open 197553/1986, Japanese Patent Application Laid-Open 271270/1986, Japanese Patent Application Laid-Open 57565/1988, Japanese Patent Application Laid-Open 272566/1989, Japanese Patent for Laid-Open 156953/1989, Japanese Patent Application Laid-Open 72151/1990, Japanese Patent Application Laid-Open 96560/1990, Japanese Patent Application Laid-Open 231465/1990, Japanese Patent Application Laid-Open 212467/1990, Japanese Patent Application Laid-Open 54161/1992, Japanese Patent Application Laid-Open 145060/1992,
The reaction of sulfonamide bodies (IX) with compounds (X) are usually carried out both with or without solvent.
As the solvent, in cases where it is used, there can be mentioned, for example, hydrocarobons such as petrol ether, pentane, hexane, cyclohexane, benzene, toluene, xylene, and so on, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,2-dichloroethylene, trichloroethylene, chlorobenzene, and so on, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, ethyleneglycol monomethylether, diethyleneglycol dimethylether, and so on, esters such as ethyl acetate, butyl acetate, and so on, ketones such as acetone, methyl ethyl ketone, and so on, nitrites such as acetonitrile, propionitrile, and so on, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and so on, sulfoxides such as dimethylsulfoxide, and so on, sulfones such as sulfolan, and so on, nitro compounds such as nitromethane, nitrobenzene, and so on, alcohols such as methanol, ethanol, isopropanol, 1-butanol, ethylene glycol, and so on, carbon disulfide, water, and so on.
The reaction can be carried out at temperatures selected from xe2x88x92100 to 300xc2x0 C., or more preferably from xe2x88x9250 to 200xc2x0 C. The reaction time is 1 minute to 1 week, or more preferably 5 minutes to 24 hours.
Acids or bases may be added to promote the reaction. As the acids employable for that purpose, there can be mentioned, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, nitric acid, perchloric acid, and organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, tartaric acid, malic acid, oxalic acid, succinic acid, benzoic acid, picric acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, and so on.
As the bases employable, there can be mentioned, for example, metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and so on, metal carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, and so on, metal hydrides such as sodium hydride, potassium hydride, carcium hydride, and so on, metal amides such as lithium diisopropylamide, sodium amide, potassium amide, and so on, organolithium reagents such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, phenyllithium, and so on, organo-magnesium reagents (Grignard reagent) such as methylmagnesium bromide, ethylmagnesium chloride, and so on, metals such as lithium metal, sodium metal, potassium methal, and so on, organic bases such as trimethylamine, triethylamine, diisopropylamine, N,N-dimethyaniline, pyridine, lutidine, collidine, DMAP (4-dimethylaminopyridine), TMEDA (tetramethylethylenediamine), DBU (1,8-diazacyclo[5.4.0]undec-7-ene), and so on.
Further, in order to promote the reaction, metal salts (for example, oxides, fluorides, chlorides, bromides, iodides, sulfides, sulfates, nitrates, phosphates, perchlorate, and so on) or metal elements of titanium, vanadium, chromium, manganum, iron, cobalt, nickel,copper, zinc, zilconium, niobium, molybdenum, ruthenium, rhodium, palladium, silver, cadmium, tungsten , platinum, gold, mercury, and so on, can be used as catalyst in an amount of 0.000001 to 1000 equivalents, or more preferably 0.001 to 10 equivalents.
The reactions of sulfonamide bodies (XI) with electrophiles are usually carried out with or without solvent.
As the solvent, in cases where it is employed, there can be mentioned those solvents which can be employed in reaction {circle around (2)} above. The reactions can be carried out at temperatures of xe2x88x92100 to 300xc2x0 C., or more preferably at xe2x88x9250 to 200xc2x0 C. And the reaction time is from 1 minutes to 1 week, or more preferably from 5 minutes to 24 hours. Acids and bases may be added to promote the reaction, and as such acids and bases, there can be mentioned the same ones as mentioned in reaction {circle around (2)} above also here.
Further, in order to promote the reaction, metal salts (for example, oxides, fluorides, chlorides, bromides, iodides, sulfides, sulfates, nitrates, phosphates, perchlorate, and so on) or metal elements of titanium, vanadium, chromium, manganum, iron, cobalt, nickel,copper,zinc, zilconium, niobium, molybdenum, ruthenium, rhodium, palladium, silver, cadmium, tungsten (wolfram), platinum, gold, mercury, and so on, can be used as catalyst in an amount of 0.000001 to 1000 equivalents, or more preferably 0.001 to 10 equivalents. The electrophiles (XII) can be used even in a large excess, unless they have an effect wrongly on the reaction of sulfonamides (XI). However, it is usually preferable to use 1.0 to 10 equivalents of them. As such electrophiles, there can be mentioned, for example, halogenides such as methyl iodide, ethyl iodide, propyl bromide, propyl iodide, isopropyl idodide, cyclopropyl bromide, butyl bromide, isobutyl bromide, allyl chloride, allyl bromide, propargyl bromide, 1,2-dibromoethane, acetyl chloride, propargyl chloride, methyl chloro-formate, ethyl chloroformate, methanesulfonyl chloride, benzene-sulfonyl chloride, p-toluenesulfonyl chloride, and so on, sulfuric acid esters such as dimethyl sulfate, diethyl sulfate, and so on, sulfuric acid esters such as dimethyl sulfate, diethyl sulfate, and so on, sulfonates such as methyl methanesulfonate, ethyl benzenesulfonate, isopropyl p-toluenesulfonate, and so on, and acid anhydrides such as acetic anhydride, trifluoroacetic acid anhydride, trifluoromethane-sulfonic acid anhydride, mixed anhydride of acetic acid-formic acid, and so on.

Compound (I0) or salts thereof can be obtained by reacting sulfonylating agents represented by Formula (VII) mentioned above, with amines represented by the Formula (XIII) (wherein symbols have the same meanings as mentioned above) or salts thereof.
The reactions of this type are usually carried out with or without solvent. As the solvent which is employable in reactions with solvent, there can be mentioned those mentioned in (A) {circle around (2)} above. The reaction temperature is xe2x88x92100 to 300xc2x0 C., or more preferably xe2x88x9250 to 200xc2x0 C., and the reaction time is from 1 minutes to 1 week, or, more preferably from 5 minutes to 24 hours. Acids and bases may be added to promote the reaction, and as those acids and bases, there can be mentioned the same ones as those mentioned above regarding the reaction equation (A) {circle around (2)} described above. Furthermore, in order to promote the reaction, metal salts (for example, oxides, fluorides, chlorides, bromides, iodides, sulfides, sulfates, nitrates, phosphates, perchlorate, and so on) or metal elements of titanium. vanadium. chromium, manganum, iron, cobalt, nickel,copper, zinc, zilconium, niobium, molybdenum, ruthenium, rhodium, palladium, silver, cadmium, tungsten, platinum, gold, mercury, and so on, can be added as catalyst in an amount of 0.000001 to 1000 equivalents, or more preferably 0.001 to 10 equivalents.

Compound (I0) or salts thereof can be obtained by reacting sulfonamides represented by Formula XIV (wherein each symbol has the same meaning as mentioned before) or salts thereof, with compounds represented by the Formula (X) above or salts thereof.
A0xe2x80x94X0xe2x80x94SO2xe2x80x94NHZ0xe2x80x83xe2x80x83(XIV):
This kind of reaction is carried out usually with or without solvent. As the solvent which is employable in reactions using solvent, there can be mentioned those described in (A) {circle around (2)} above. The reaction temperature is xe2x88x92100 to 300xc2x0 C., or more preferably at xe2x88x9250 to 200xc2x0 C., and the reaction time is from 1 minutes to 1 week, or more preferably from 5 minutes to 24 hours. Acids and bases may be added to promote the reaction, and as for those acids and bases, there may be mentioned the same ones as those mentioned above regarding the reaction equation (A) {circle around (2)}. Further, in order to promote the reaction, metal salts (for example, oxides, fluorides, chlorides, bromides, iodides, sulfides, sulfates, nitrates, phosphates, perchlorate, and so on) or metal elements of titanium. vanadium. chromium, manganum, iron, cobalt, nickel,copper, zinc, zilconium, niobium, molybdenum, ruthenium, rhodium, palladium, silver, cadmium, tungsten, platinum, gold, mercury, and so on, can be added as catalyst in an amount of 0.000001 to 1000 equivalents, or more preferably 0.001 to 10 equivalents.
When compounds (VII) to (XIV) are in the forms of salts, they can be in the types of the salt similar to those mentioned concerning compound (I0)
When compound (I0) or salts thereof have nitro groups as the substituent in B0, they can be obtained by nitrating the corresponding raw-material (compounds which have no substituents at the positions where the nitro substitution will be introduced) with nitrating agents [synthetic method (D)]. As nitrating agents, 30 to 100% nitric acids and fuming nitric acids are commonly used. However, other nitrating agents such as alkali metal nitrates, for example, sodium nitrate, potassium nitrate, and so on, alkyl ester nitrates such as ethyl nitrate, amyl nitrate, and so on, nitronium tetrafluoroborate (NO2BF4), nitronium trifluoromethanesulfonate (NO2CF3SO3), nitrogen oxides (for example, NO2, N2O3, N2O4, N2O5), and so on. Fifty to 100% nitric acids are especially preferable. The nitrating agents may be used about in 1.0 to 20 equivalents to the raw-material which is not substituted at positions where nitro substitution will occur. More preferably, the ratio of nitrating agent to the raw material is 1.0 to 10 equivalents, or about 1.0 to 3.0 equivalents in cases where nitric acid of 90% or so is used.
Although the nitration reaction may be carried out in the absence of solvent, it is usually done in the presence of acidic solvents such as sulfuric acid, acetic acid, acetic anhydride, trifluoroacetic acid anhydride, trifluoromethane sulfonic acid, and so on. If it is desirable, any solvents or mixtures of solvents which do not affect wrongly to the reaction can be used. As such solvents, there can be mentioned, in addition to the acidic solvents mentioned above, those solvents described regarding the reaction (A) {circle around (2)} above. Those solvents can either be used singly, or, if necessary, as mixtures of two or more (preferably 2 to 3) species of them together, in appropriate ratios of, for example, about 1:1 to 1:10 (v/v ratios).
In the cases where the reaction solvent is not homogeneous, the reaction may be made in the presence of phase-transfer-catalysts, for example, quaternary ammonium salts such as triethylbenzyl-ammonium chloride, tri-n-octylmethylammonium chloride, trimethyl-decylammonium chloride, tetramethylammonium bromide, cetyl-pyridinium bromide, and so on, and crown ethers, and so on.
The most preferable solvents are acetic acid and acetic anhydride. The reaction temperature is usually about xe2x88x9250 to 200xc2x0 C., more preferably about xe2x88x9220 to 130xc2x0 C., and the reaction time is from about 1 mimute to 24 hours, more preferably from about 15 minutes to 3 hours.
Here, the compound (VI) or salts thereof can be prepared according to the method (D) above, thus, for example, by nitrating the compounds which may be represented by the Formula 
(where B7 is a phenyl group which is substituted with substituents selected from halogen atoms (for example, fluorine, chlorine, bromine, iodine), nitro, and cyano, but at least one of the 2- and 6-positions is remained unsubstituted), and other symbols have the same meanings as mentioned above) or satls thereof.
The xe2x80x9cphenyl group of which at least one of the 2- and 6-positions is remained unsubstitutedxe2x80x9d in B6 can be substituted with substituents selected from halogen atoms, nitro, and cyano, and the number of substituents can be 1 to 3.
In the cases where compound (I0) or salts thereof have substituents, those substituents can either be introduced in advance at the stage of the raw material or the intermediates (VII) to (XIV), or necessary sabstituents can be introduced or converted into afterward, after synthesizing compound (I0) or salts thereof, by means of known methods for converting functional groups following the methods describedin, for example, Organic Reactions, Organic Syntheses, Synthetic Methods of Organic Chemistry, Compendium of Organic Synthetic Methods), and so on.
As such substituent convertion reactions, there may be mentioned, for example, the synthetic methods of (E) to (T) which will be followed, but these are only examples and the methods applicable, and should not be considered to be restricted to them.
Those compounds which have alkylthio groups and can be prepared from known raw materials according to the reaction equations (A), (B) or (C), may be converted into compounds which have alkylsulfinyl groups by reacting them with 0.5 to 2.0 equivalents, or more preferably with 0.8 to 1.5 equivalents of appropriate oxidating agent (for example, hydrogen peroxide, peracetic acid, perbenzoic acid, meta-chloroperbenzoic acid, potassium permanganate). Similarly, but with 1.5 or more equivalents, or more preferably, with 2.0 to 3.0 equivalents of oxidating agents, the compounds which have alkylthio groups which have alkylsulfonyl groups can be converted into the corresponding alkylsulfonyl compounds.
Those compounds which have alkoxycarbonyl groups and can be prepared from known raw materials according to the reaction equations (A), (B) or (C), may be converted into compounds having carboxyl groups by subjecting them to hydrolysis reaction in the presence of bases (for example, sodium hydroxide, potassium hydroxide, and so on) or acids (for example, sulfuric acid, hydrochloric acid, and so on).
Those compounds which have carboxyl groups, can be esterified by reacting them with alcohols (for example, methanol, ethanol, and so on), in the presence of appropriate acids (for example, sulfuric acid, p-toluenesulfonic acid, and so on). Further, the carboxyl groups can be converted into compounds which have esters or amides by first activating the carboxyl groups (for example, by converting it (them) into acid chloride with thionyl chloride or phosphorus oxychloride, by converting it (them) into acid anhydride with carboxylic chloride,chlorofolmic ester by activating it (them) with dicyclohexylcarbodiimide, methylpyridinium chloride, and so on), and then by reacting the products with alcohols or amines, respectively.
Compounds having amide (CONH2) groups can be converted into compounds having cyano groups by reacting the former compounds with dehydrating agents (for example, acetic anhydride, trifluoroacetic acid anhydride, thionyl chloride, phosphorus oxychloride, phosphorus pentoxide, and so on) in the presence or absence of bases (for example, pyridine, triethylamine, and so on).
Compounds having amide groups can be converted into compounds with thioamide groups by reacting the amide compounds with Lawesson""s Reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-di-phosphetane-2,4-di sulfide) or with phosphorus pentasulfide, those compounds having cayno groups can be converted into compounds having thioamide groups by adding hydrogen sulfide to the cyano groups.
Compounds with carboxyl groups prepared by the synthetic method (F), and so on, compounds with ester groups or amide groups prepared by the synthetic method (G), and so on, or compounds with cyano groups prepared by the synthetic method (H), and so on, can be converted to compounds with formyl groups by subjecting them to reduction reaction with appropriate reducing agents (for example, catalytic hydrogenation, diborane, silanes, sodium borohydride, lithium aluminum hydride, diisobutyl aluminum, and so on), or compounds with methyl groups or hydroxymethyl groups prepared by the synthetic methods of (A) to (C) can be converted into compounds with formyl groups by oxidizing them with oxidizing agents (for example, chromic acids, dichromates, manganum dioxide, potassium permanganate, selenium dioxide, dimethylsulfoxide-oxalyl chloride-triethylamine [Swern oxidation], and so on).
Compounds (compounds unsubstituted at positions where formyl group can be Introduced) which can be prepared from known raw material accoding to the methods shown by the reaction equations (A), (B) or (C) can be converted into compounds with formyl groups by formulating them with formylating agents (for example, phosphorus oxychloride-N,N-dimethylformamide [Vilsmeier reaction], zinc chloride-hydrogen cyanide-hydrogen chloride [Gattermann reaction], chloroform-sodium hydroxide [Reimer-Tiemann reaction] and dichloromethoxyethane-aluminum chloride, and so on).
Oximes and hydrazones can be prepared from compounds with formyl groups which can be prepared by the synthetic methods (J) or (K), by reacting them with hydroxylamines or hydrazines, respectively.
Compounds with haloalkyl groups can be converted to compounds with various functional group by making them to react with appropriate nucleophiles (for example, mercaptanes such as methyl mercaptane, ethyl mercaptane, and so on, amines such as ammonia, methylamine, dimethylamine, and so on, alcohols such as methanol, ethanol, and so on) in the presence of appropriate bases (for example, sodium hydroxide sodium hydride, sodium carbonate, potassium carbonate, and so on).
Compounds with haloethyl group which can be prepared from known raw material accoding to the methods shown by the reaction equations (A), (B) or (C) can be converted into compounds with vinyl groups by subjecting them to dehydrohalogenation reaction with bases.
Compounds with terminal acetylene group which can be prepared from known raw material accoding to the methods shown by the reaction equations (A), (B) or (C) can be converted into compounds with haloacetylene groups by making them to react with halogen sorces (for example, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, chlorine, bromine,iodine, and so on) in the presence of appropriate bases (for example, sodium hydroxide, sodium hydride, sodium carbonate, potassium carbonate, n-butyllithium, and so on).
Compounds with nitro groups which can be obtained according to the reaction equation (A), (B), or (C), or the synthetic method (D), can be converted into compounds with amino groups by making them to react with reducing agents (for example, catalytic hydrogenation, iron, tin, zinc, ferrous chloride, stannous chloride, and so on).
Compounds with amino groups which can be synthesized by the synthetic method (P), and so on, may be converted to compounds with nitroso groups by making them to react with oxidizing agents (for example, hydrogen peroxide, peracetic acid, perbenzoic acid, meta-chloro-perbenzoic acid, potassium permanganate, and so on).
Compounds with nitroso groups which can be prepared by the synthetic method (Q), and so on, may be converted to compounds with azoxycyano groups by making them to react first with N-oxidizing agents (for example, N-chlorosuccinimide, N-bromosuccinimide, iodobenzene diacetate, and so on), and then with cyanamide in the presence of bases (for example, sodium carbonate, potassium carbonate, sodium hydroxide, and so on).
Compounds with hydroxy groups protected with a protecting group (for example, methoxymethyl group, dihydropyranyl group, acetyl group, methoxycarbonyl group, benzyl group, tert-butylmethylsilyl group, and so on) which can be produced from known raw materials according to the reaction equation (A), (B), or (C), can be converted into compounds with hydroxyl groups by subjecting them to deprotection reactions according to the method described in, for example, xe2x80x9cProtective Groups in Organic Synthesisxe2x80x9d, and so on.
Compounds with hydroxy groups which can be prepared by the synthetic method s, and so on, may be converted to compounds with various substituents by making them to react with electrophiles (for example, methyl iodide, dimethyl sulfate, ethyl iodide, isopropyl iodide, propyl bromide, 1,2-dibromo ethane, acetic anhydride, acetyl chloride, methyl chloroformate, trifluoroacetic anhydride, methanesulfonyl chloride, p-toluenesulfonyl chloride, and so on), e.g., by means of substitution reactions, in the presence of appropriate bases (for example, sodium hydroxide, sodium hydride, sodium carbonate, potassium carbonate, and so on).
Hereunder, the present invention is illustrated in more detail by reference to the following Examples, Formulation Examples, and Test Examples. However, the scope of the compound (I0) or salts thereof is not to be considered to be restricted to the present embodiment.
In the synthesis examples, elution in silica gel column chromatography was carried out under observation by means of TLC (Thin Layer Chromatography). In the TLC-observation, the Kieselgel 60F254 (70-230 mesh) plates manufactured by Merck and Co., were used as the TLC-plate, and as the eluents used were the same solvent as that used in the column chromatography as eluent, and as the detection method, either the UV-detector or coloration method with iodine was adopted. As silica gel for the column chromatography, Kieselgel 60 (70-230 mesh) manufactured by Merck and Co. was used.
When a mixed solvent was used as eluent, the ratio shown in the ( ) indicates the volume to volume ratio of the solvents mixed. NMR (Nuclear Magnetic Resonance) spectrum means the proton NMR, and was measured by a Bruker AC-200P type (200 MHz) spectrometer, using tetramethylsilane as internal standard. All xcex4 values are in ppm. Abbreviations used in the Reference Examples, Examples and Tables below have the meanings which follow, s: singlet, d: doublet, t: triplet, q: quartet, m: multiplet, dd: double doublet, dt: double triplet, dq: double quartet, septet: septet(a set of seven lines), br: broad, brs: broad singlet, ddd: double double doublet, ddt: double double triplet, brd: broad doublet, brq: broad quartet, J: coupling constant, JHF: coupling constant of the coupling between hydrogen atom and fluorine atom, Hz: Heltz, CDCl3: deutero-chloroform (chloroform-d), DMSO-d6: dimethyl sulfoxide-d6, DMF: N,N-dimethylformamide, %: wt %, and mp: melting point. In addition, room temperature means a temperature or temperatures within 15-25xc2x0 C.